


Babysitting

by KaizerUwU



Category: Pocket Monsters | Pokemon (Anime), Pocket Monsters | Pokemon (Main Video Game Series), Pocket Monsters | Pokemon - All Media Types
Genre: Cub, Fluff and Smut, Foursome - F/F/F/M, Multi, NSFW, Oral Sex, Pokephilia, Sex, Threesome - F/F/M, Vaginal Fingering, Vaginal Sex
Language: English
Status: In-Progress
Published: 2019-07-19
Updated: 2019-07-19
Packaged: 2020-07-08 22:39:39
Rating: Explicit
Warnings: Underage
Chapters: 2
Words: 27,549
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19877230
Author URL: https://archiveofourown.org/users/KaizerUwU/pseuds/KaizerUwU
Summary: Cole is hired to babysit a few pokemon. While he is, things turn a bit sexual when they start getting messy. After watching the first few, he decides he wants to start babysitting more where even more join in on the fun.





	1. Chapter 1

**Author's Note:**

  * For [OtherThatGuy](https://archiveofourown.org/users/OtherThatGuy/gifts).



> Commission Story part one for OtherThatGuy. Uploading from old account. Can't remember every detail so sorry if things aren't properly tagged.
> 
> Join my Discord! Discord dot gg slash DdtXZtX

Cole sat idly on his couch, watching the television show some random program. It was some program people that quickly made him lose interest. The only reason he was was watching it was because he had time to kill. He had a job today for a bit of spare cash and he didn’t need to be there for another half hour. So he decided to just watch something to kill time, which ended up being a stupid idea since it was hardly even doing that. “I fucking hate television,” he grumbled.

Deciding he might as well get there earlier than later to hopefully get a rundown of how things were, Cole got up and quickly got changed. As he he did, he thought about what he would need to bring for the job. Babysitting pokémon was something he’d never done before but it didn’t seem too difficult. He absolutely loved being with them, so why would it be hard? Surely, it wouldn’t be, right? The only difficult part of it would be that he’d never worked with a smeargle or riolu before. Other than that, all he had to do was make them lunch and play with them, both of which was no problem. Deep down, Cole looked forward to playing with them. That would be a lot of fun!

Thankfully for Cole, the person who needed their pokémon babysat was actually a neighbor. She lived in the same subdivision but not directly next to him. So the walk to her home wasn’t a long one at all, ten minutes max. Once there, he rang the doorbell and waited. A few moments later, he heard the lock of the door being messed with, where a rather pretty lady stood on the opposite side once opened. “Oh, hey Cole. You’re early,” she said. She held the door open for him, allowing him to come in.

“I hope that’s fine. I had left a bit earlier than I thought. Was an accident. Hope you don’t mind,” he lied with a chuckle following after. He looked around as he followed her, admiring the beautiful decorations she had. She had cabinets with fragile china in them, beautiful paintings of her two pokémon hanging from the walls, and rugs lining almost the entire floor. It struck him as odd since most of the floor was hardwood, but he couldn’t judge. It wasn’t his house.

“That’s no problem at all. Tori! Sara! Come here!” the lady yelled out. Cole heard the sound of tiny paws and giggling down a hallway just behind the girl. “They’re both a bundle of energy. I hope that’s no problem for you!”

“Not at all. I’m sure I’ll get them all tuckered out for you by the time you get back,” he said with a chuckle. The two pokémon they were talking about both bolted into the kitchen moments later, big smiles on their face.

“Yeah, mom?” the riolu said. It didn’t see Cole until it got in the kitchen. When it did, it immediately stopped and eyed him curiously. The smeargle also noticed him but, unlike the riolu, hid behind the girl nervously. “Is he our new friend you told us about?” asked the riolu in the same curious tone.

“Yes he is. Cole, this is Tori,” she said, motioning to the curious riolu. The riolu quickly jumped up on the counter and padded over to him. When she got close enough, she waved excitedly before holding a paw out to him.

“Hi!” she exclaimed. Cole found her enthusiasm to be quite funny. He graciously reached out and shook the pokémon’s paw, making her smile brightly. 

“Hello to you too,” he said.

“Tori is the outspoken one of the two. This is Sara,” she said, now motioning to the smeargle. The pokémon held its tail tightly as it barely peaked around her human’s legs. Cole didn’t want to frighten her so he squatted down and held a hand out for her, just as he did for Tori. The pokémon recoiled fearfully in response. “She’s super timid at first. Give her a few minutes and she’ll warm up quickly,” explained the girl.

“I understand entirely,” he said. Tori jumped back from the counter and ran over to the smeargle where she grabbed its paw.

“Mom, can we paint? Sara was saying she wants to,” Tori asked. 

“Are you two going to make a mess again?” she asked the two. They immediately shook their heads no but she didn’t believe it. “They love to paint. Sara is obviously a natural artist but she’s still not used to her tail. She’s constantly getting things dirty, aren’t you?” she said, eyeing the smeargle. She nodded slowly, not saying anything. “Take a seat Cole,” she said, nodding to the table. “Any reason you came early, besides on accident?” she asked as she grabbed the stuff for the girls to paint.

“I was hoping you’d be able to like… show me the ropes or something like that,” he said as he walked over to the table and took a seat. “You know, tell me what I need to know and all that.”

“Sure, that’s no problem! So, first off, they’re balls of energy as I mentioned. Sometimes it can get a bit overwhelming. If it ever does, you’re more than able to tell them to go play together in their rooms. Trust me, with these two, they’ll get you worked up all right,” she began explaining. Cole nodded with a chuckle as the two ran to the table. Tori immediately jumped in a chair next to Cole, opting to sit by him. Sara on the other hand ran over but stopped. She looked at the chairs for a moment before quickly jumping into Cole’s lap, catching him off-guard. 

“Look Mom! Sara likes him!” Tori exclaimed.

“Shut up!” Sara yelled back immediately. The girl turned around and saw Sara sitting in Cole’s lap. 

“...Did she jump there on her own?” she asked as she walked over. Cole saw small books in her hands with large pictures on them. He knew they were coloring books for the two cubs. 

“Yeah, she did. I don’t mind. If she’s comfortable with it, then it won’t bug me,” he said with a smile. The smeargle looked up at him before smiling slightly. He smiled back to her and rested a hand on her leg, making her tense but she quickly relaxed to the touch.

“Well that’s good she warmed up to you quick. They’ll both like your company,” she said as she laid out the books for the two. The two immediately opened them and found the pages they wanted to color and paint. “Especially Sara. I think you’ll like her a lot,” she smiled to the two pokémon.

“They’re both very cute pokémon,” he said as he continue gently petting the smeargle’s leg. She brought her tail up and wrapped it around his arm, holding him where he was as she began painting. Her head barely poked over the table, making it hard for her to see. She looked over to Tori and saw her standing in her chair, making it easier. “You can stand in my lap, I don’t mind,” he told her. Sara smiled graciously to him. 

“Thanks!” she said. He grabbed her by the waist and helped her stand up. She had a paw on each of his thighs, giving her the height she needed to be able to see. 

“So, food. For your safety, avoid giving them sugar. I learned the hard way if you give them it one time, they’ll never sit still. They’ll keep begging for more after, so don’t do that for your safety. I’ve got meals already made in the fridge, you just need to heat them up,” explained the girl. She then walked over to the fridge and opened it before pulling out two cups with lids for the girls, both of which looked like they were filled with juice of some kind. “Tori can’t have Oran Berries, so we give her Sitrus Berry juice. Sara, on the other hand, love Oran Berry juice. Want her to sit still? Give her some of that and you’re golden.”

“Oh, that’s interesting,” he said, taking in the information. He continued petting the smeargle as she painted. He tried to peak over her shoulder and look at what she was doing but the pokémon immediately covered the drawing with her paws.

“No peeking! It’s a surprise!” she yelled at him. Cole immediately looked away, not wanting to ruin her ‘surprise’ for him. Sara stepped around in his lap as she went back to coloring. She didn’t know it, but she continuously stepped gently on his crotch and directly on where his privates were. She was super gently and it almost felt like she was rubbing against his crotch. 

Woah there, Bucko, let’s stop those thoughts. That is all kinds of fucked up, he thought to himself. He took a deep breath and went back to petting her back, pushing those perverted thoughts to the side. He looked down at her and felt how she was leaning more into his touch as his hand went lower down her back. In the most non-weird way I can say this, for a cub, she has a really big butt… 

“For food, they can eat almost anything. Of course, like I mentioned, avoid sugar. Rest is fair game. If they get hungry before lunch, you can give them a snack,” the girl went back to explaining. Cole found it hard to listen to her as Sara kept stepping and rubbing right over his growing member. At first, she must not have known but as time went on, she grew curious at what she kept stepping on because she looked down at his lap curiously.

“What’s-.”

“It’s my phone,” he interrupted quickly. He knew exactly what she was going to refer to and needed to keep that conversation away. Reaching into his pocket, Cole pulled out his phone and moved Sara so she wasn’t stepping on his bulge anymore, as much as he wanted her to. It was so gentle, like she knew. I wonder how gentle her paws… Fucking stop it dude, what the fuck? “See?” he told her.

“Oh! That looks like Mommy’s!” she exclaimed. She grabbed it from his hand and held it up to the girl, who nodded.

“Yep, it is. Come on, put it down before you accidently drop it,” the girl said. Sara nodded and put it down on the table before going back to her painting. “All in all, they’re both really easy to take care of. However, there’s one thing about Sara you need to know and I should have warned you about,” she said. Cole eyed her curiously as she continued, “Like I said, she’s still getting used to the paint coming from her tail. She often times doesn’t realize it but she drips a lot so you may have to clean yourself, and her, quite often. Before you feed them lunch, I’d really like if you washed them both.”

“So you want me to bathe them?” he asked for clarification. 

“I’d greatly appreciate it, yes. It’s a habit I’ve started and I’d like it to be followed. I have all their cleaning stuff in the bathroom and they know where everything is, too. So it shouldn’t be a problem for you,” she told him.

“That’s fine with me. I figured a mess could be expected so I wore some old clothes. I’ve never worked with smeargle before but I figured their little artistic abilities would come out at a young age. Which reminds me, how old are they?” asked Cole curiously.

“They’re both a half-year old. So they’re not babies still in the classical sense, but they’re still considered cubs,” she answered. Cole nodded and right after answering, the girls phone gave off an annoying ring. “And that’s my alarm. I gotta head out to work now. Thanks again for doing this. I’ll give you your money tonight!” she said. 

“It’s okay. Glad to help out and get the experience. I’d love to work with pokémon so this helps me a lot,” he said with a smile. The girl nodded and grabbed her purse off the counter. She dug through it momentarily before pulling out her keys. “Okay girls, come give mommy a hug!” she said. The two pokémon quickly jumped from where they sat and ran over to her and jumped in her arms. “Be good to Cole, okay? I don’t wanna come back and hear you both got in trouble.”

“We will! We promise!” they said in unison. She nodded and looked up to Cole.

“Let me know if you need anything. I’ll be back around eight,” she told him.

“Alright. Have a good day,” he said with a smile. Sara quickly ran over and jumped back in his lap. This time, she sat back and and sat with her back against his belly. She scooted around for a short time, continuously rubbing against his previously-dying erection. F-fuck, that is so wrong to enjoy, he thought to himself. The tiny motions weren’t enough to drive him mad, but they did feel pretty nice. He wrapped an arm around her belly and held her still, trying to fight back the weird thoughts that were growing.

With a wave, the girl turned around and exited through a door in another room, leaving the girls in his protection. “Here you go!” Sara exclaimed, catching his attention. He looked down to her and saw her reach forward to the paper. He didn’t notice right away but the painting was done. Though crude, he got the idea of it. “For you!”

“Well I can see someone is learning very quick!” he told her. The drawing was a stick figure with a paw print next to it. Arrows pointed the figure and it had his name above them, showing her was the figure. 

“The paw is mine! See?” she said, showing him her paw. Her paw was covered in bright green ink, like the picture. How had nobody noticed?

“Well I’ll be, it sure is yours. Let’s get your paw cleaned real quick. Don’t wanna get you too messy,” he told her.

“Okay,” she nodded. Cole held her tightly as he picked her up and over to the counter. He then grabbed a paper towel and ran it under the water coming from the sink. 

“Now let’s see that paw,” he told her. She held it out to him where he gently gripped it and wiped it clean. “There, all clean. I forgot to ask your mom but does she ever wipe the paint off your tail if it’s dripping?”

“She does! She always done when I’m done making a picture or it’ll keep dripping and drip faster,” explained the small pokémon. 

“Do you want to keep painting?” he asked her.

“Can you play blocks with us?” Tori spoke up.

“Yeah! Come play blocks with us!” she told him hopefully. He chuckled and nodded.

“Okay, but let me clean off your tail a bit first. Then you two can show me how to play blocks,” he told them. He saw Sara’s tail hanging above her head, dripping slowly as she stood there. She slowly brought it over to him, where it dripped a few times down her body. 

“Oops… Sorry…” she said, realizing she made a mess on herself. He smiled and patted her shoulder.

“Don’t be upset. Accidents happen. We’ll get you cleaned up quickly. Go ahead and sit down,” he told her. She perked up quickly that she wasn’t in trouble and did as asked. He threw away the already dirty rag and grabbed another, repeating the actions to get it wet. He quickly wiped up the paint from her shoulder and belly, looking over the rest of her to see if it was anywhere else. The lower he got, the more his mind went dirty. Come on… it’s just cleaning… Don’t be perverted about it… “Let me see your legs,” he told her.

Cole rested a hand on her leg and saw no paint on them on the top. He knew he had to check between her legs so he gently spread them, giving him a view he’d have much rather have not seen. He was mere inches from her slit and to say it was inviting was an understatement. He wanted to not keep looking but he found it hard not to. “Is there any down there?” she asked curiously. He took a deep breath, happy to have had her speak up so he could look away.

“No, thankfully not. You’re all clean,” he told her. Cole looked up to her and she smiled at him.

“Yay! But why is your face red? Are you sick?” she asked worriedly. 

“No, I’m not. I promise,” he told her reassuringly.

“Okay… Well, that’s good!” she smiled instantly after. He smiled back and rubbed the top of her head, enjoying the soft fur on top. 

“Umm… Cole?” Tori spoke up. He looked over to her as she tugged on his pants leg. “I dropped my brush and got paint on me…”

“That’s okay. We’ll get you cleaned up quick. Sara, why not get your blocks ready?” he asked her. She nodded enthusiastically and jumped from the counter.

“Okay! Hurry up!” she told him before running to the room they came from when he got there. Cole threw away the second dirtied paper towel and got a new one. As he did, Tori sat down on the counter just like Sara was moments ago. 

“So where’s that mess?” he asked her. Like Sara, she spread her legs wide for him, giving him a view of her privates. Her slit was incredibly small but looked even more inviting. She had paint trailing her inner thigh and close to her slit. Just above it her folds was a tiny drop of paint where it looked like it fell. “O-oh…”

Fuck. Come on, you can not be weird about this…

“Sorry… I was excited about blocks and it just… fell…”

“Don’t worry, Tori. It happens. Just be more careful next time, okay?” he told her. She nodded slowly but she didn’t perk up like Sara did. Cole thought for a moment on the best way to go about it. He knew he was going to have to clean her but to do it without feeling weird was going to be impossible. ...Maybe… just… one touch and I’ll be good… he thought to himself. He hated he just thought that but the way she was showing herself off without realizing made it hard not to want to.

“I will be. Promise,” she told him. He smiled and reached for a third and final paper towel. He wet it and quickly wiped up the paint on her thigh, leaving the bit just above her slit. He slowly reached forward and cleaned it off. He was so close to it that it made it even more difficult. He looked up at her and saw the curious look she had. Okay… Just one… I swear… he told himself. He reached back between her legs and rested a finger against her slit. Again, he looked up at her to see her expression, but it was just as curious. Slowly, he trailed his pointer finger from the bottom of her slit to the top, gently poking his finger in as he did. When he got to the top of her slit, he gently rubbed the tiny nub she had, where he felt a positive shiver in response from her. 

“What was that?” she asked him curiously. She looked between her legs as he pulled his hand away. He sighed inwardly. He expected to be better but the feeling of her shivering against his touch made him want to do it again. 

“I just had to clean you,” he lied. He knew exactly what he was doing but had to play it off. “Why?”

“It… felt good. Can you do it one more time?” she asked. 

Fucking fuck fuck. Why did I do that?

Now he wanted to take it a step further. If he could touch her like that and she didn’t respond negatively, how far could he go? Maybe… he could test it. “Do what again?” he asked her. He knew what, but he wanted to hear her say it himself. 

“Clean me like that. Mommy never has and I liked it how you did,” she told him. He was in a battle with himself now. He told himself one time but now she wanted it. It was so wrong, but did it feel so right. He had to see how far he could go before she got uncomfortable. 

I wonder… how she’d taste… he wondered. It was beyond wrong of him to even consider that of her but he had to find out. So he gently held her legs spread open for him. The view was beautiful and one he didn’t want to look away from. Slowly, Cole leaned forward until he was face to face with her slit. Then, he stuck his tongue out and ran it along the length of her slit. Like before he felt her shiver positively against his touch. The taste was of berries and from that one lick, though it was only a little bit there, he wanted more. But he told himself only one time to see. He pulled himself free, where a whine almost came from Tori. “There, all clean,” he said with a small blush. 

“T-that felt good. Can you keep doing that?” she asked him with big, puppy eyes. He cursed to himself as he stood up. The temptation was so unreal but he knew it was better to stop there. He got what he wanted and knew it would be a bad idea to keep going. 

“And keep Sara waiting? Come on, let’s go play with her,” he said, getting her mind off it. Immediately, she perked up and nodded enthusiastically. 

“Okay! Come on!” she yelled as she jumped off the counter. She crouched over with her tail raised high, ready to run to her room. He looked at her behind immediately, followed by her tiny slit. He saw it was a tiny bit wet and even more inviting than ever. She ran ahead to her room, leaving Cole to himself.

“What the fuck am I getting myself into…” he mumbled. He walked over to the table and grabbed his phone before putting it in his pocket. He then walked down the hall towards the girls’ room. Being one of the two rooms in the hallway, it wasn’t hard to find it. He walked in and saw just how girly it was, which obviously made sense. It was painted a bright pink with brighter pink floral stickers all over the wall. A singular bed rested against the wall with both their names on the bed frame in pretty letters. An easel was against one wall with Sara’s name on it. It made sense with her just now getting used to her paint. She was a smeargle after all, and art was their favorite thing ever.

Looking to the other side, he saw a large toy chest with Sara and Tori by it. “Can you help us? We can’t reach them!” Sara told him. He walked over to the chest and nodded. He got to his knees between them with Sara on the right of him.

“What am I getting?”

“Those,” Sara said. She jumped up and hung herself halfway in the chest with her behind sticking out. Her tail was raised high, giving him a view of her own privates. 

God they’re both so fucking cute… I wonder… how she’d respond… Hmmm… he thought to himself. Cole reached up and placed a hand on her butt. He then trailed a finger along her slit like he did with Sara. She instantly sighed from his touch. With a positive reaction, he did it again before sliding a finger in slightly, exactly like he did Tori.

“W-what’re you doing?” Sara asked.

“You got paint on you I had to get off,” he said, bringing his hand free. He leaned forward to try and play it off as nothing, but that action alone solidified the idea she was okay with it. He definitely had to take it further with them, and he had an idea how. He couldn’t believe he was doing this but he was too far to stop now. He already went to the point of no return, so why not go the rest of the way?

All that was left to do was wait. He had to wait until the time was right to see. With a deep breath, he reached in and grabbed the blocks for them, passing them to them as he did. Soon, he had them all out and ready to go. The two pokémon immediately took over and began building everything their little minds could come up with. They started with small towers and gradually grew into larger ones. When they got to a height they couldn’t do, they made him build higher, which he happily obliged to.

When they got bored of building towers, they started building other things their brains thought of. They were things Cole couldn’t think of but, to Sara and Tori, they were the best ideas ever. Seeing them happy made him happy, which was a win in his book. After well over two hours of building, Sara was the first to get bored and decided to go back to painting at her easel, not that it shocked him. She was an artist after all.

That left Cole with Tori. She wanted to be read to so he happily obliged. But like most children, she got bored rather quickly and wanted to play one of those ‘I Spy’ books where you have to find things and point them out to each other. That, to Cole, was much more fun. And he decided to use that as his way of exploring Tori much more than before. He had her in his lap with the book held up in front of them so Sara couldn’t see. At first, it was an innocent game to see who could find the stuff quicker. This lasted around half an hour but as time went on, he got a bit mores hands on.

It started with him just resting a hand on her belly, then each time she found what he said, he’d trail his hands lower. When he had his hands on her inner thighs, he felt her heartbeat picking up. Periodically, he would gently run his hand over her privates, giving both of them the satisfying touch they wanted. It was becoming difficult to not go as far as he really wanted, but this was just as nice. 

“Hey Tori?” Cole spoke up quietly. 

“Yeah?” she responded, looking up to him. He saw the curious and interested look in her eyes, and it drove him mad. He was so going to the Distortion World with Giratina, but it was going to be worth it to him. He was too far to stop.

“Do you like the way I’m touching you?” he asked her. Even though she would shiver every time he dragged a finger along her slit, he wanted to be sure she actually was liking it. To emphasize his point, he did it once more, only this time he slipped a finger inside of her. It only got to his first knuckle but she shook massively around his finger before nodding.

“I do. It makes me feel weird but I like that weird feeling. Is that bad?” she asked him.

“No, that’s a good thing. Would you want to help me feel that way too?” he asked her. Again, that curious stare came.

“How?” she responded. To answer, Cole gently grabbed one of her paws and rested it on the erection showing through his pants. She stayed silent, waiting for instructions.

“Do you feel that?” he asked her. She nodded to him. “Rub your paw right there slowly. If you do a good job, I’ll help you with that feeling you told me about,” he told her. She looked down at her paw then between her legs where he still had a finger in her. Once more she looked up to him before nodding. Doing as told, Tori began to move her paw against his crotch, massaging him through his shorts.

“Like this?” she asked for clarification.

“That’s perfect, good job. Keep doing that,” he told her. Wanting her to continue and hold his end of the deal, Cole pulled his finger free and began to gently rub his finger along her slit. He knew because she had never been touched in such a way, she was going to be extra sensitive to his touch. Even though he didn’t want much in return, the contact from her was nice. 

“Can… Can you…” she stuttered.

“What?” he asked her curiously. She brought the paw from his crotch and held his hand tightly. She then used the finger he was using to touch her to show him where to touch. His finger rested on the top of her slit, right where her tiny clitorus was. 

“When you touch right here, it makes me feel extra good. Well you keep touching there?” she asked of him. He was shocked at what she asked but was happy to do it. Even though he wanted to feel her touch him like she was moments ago, he wanted to see if he could get her off quickly. 

“Sit back, okay?” he told her, “Relax.” Doing as told, Tori sat back against his chest and relaxed with ease. Cole then sat up for a moment and straightened out his legs before spreading his own slightly. He sat her on the ground between them and spread her legs widely for him. “Hold the book so we can keep playing, okay?” he told her. Again, she nodded and held it in front of them.

With the book hiding what was about to happen, Cole held her legs spread open with his own legs by resting them on top. He then leaned over on top of her. “Okay, your turn,” he told her. “Find the small, red plane,” he told her. After getting a nod in response, Cole reached forward and once again began to rub her slit. She squeaked immediately and stiffened but after a few strokes, relaxed against him.

Tori began hunting for the item he told her but Cole didn’t focus on that. Instead, he went to work on trying to get her off. He knew she was young, but how old did she have to be to have her first orgasm? Surely her age was old enough since pokémon were known to have children at super young ages. The second he rubbed a finger against her sensitive nub, a shiver was sent up the small canines spine, making him smile. 

Cole didn’t want to be slow in what he was doing. He wanted to get her to cum and to do so, he had to be quick. So he continuously rubbed over her clit, tiny squeaks coming from the riolu as he did. “I-it’s right h-here,” she said, pointing out the object. 

“Good job, now find the green truck,” he told her, not even knowing if that was on the page. He wanted to keep listening to her squeak and feel her squirm against him like she was. Everytime he stroked her, she would try and squirm away, giving him a little bit of a fight. But he always prevailed as he was much stronger than her. The poor riolu had no way of fighting against him and he loved it.

As time went on and her search continued, Tori began to gently buck against his hand. He knew what that meant and it made him happy. However, he began to wonder about one thing. How messy would she be? Surely Sara would notice something like that if too messy. However, he was already too late to stop. He had to continue, and he was going to. “C-Cole?” Sara spoke up, bringing him from his thoughts.

“Yes, Tori?” he answered.

“Hey Cole? I’m getting hungry…” Sara spoke up, interrupting the two. Cole looked up from the riolu’s legs and to Sara. He smirked at how much paint she had across her body. That was a step in the right direction for him.

“Okay, we’re gonna get you two bathed and cleaned up first, okay?” he told her. The smeargle nodded to him. “Go in the bathroom and get your stuff ready. Can you do that for me?” 

“You bet I can!” she said enthusiastically. Without needing to be told twice, Sara bolted from the room and down the hall, leaving Cole and Tori to themselves. 

Perfect… 

“I… I feel… weird…” Tori panted heavily. He knew what that meant. 

“That’s good. Let that feeling happen, okay? You’ll feel a lot better after, I promise,” he told her. Cole stopped his stroking and picked her up slightly before laying her on her back. The way her laid her had her so he could see out the door in case Sara came running back. Without wasting a beat, Cole laid down with his head between her legs. “Remember what I said, okay?”

“O-okay,” she nodded. Cole leaned in and began lapping away at her folds. He had his hands forward so he could hold her arms still while he licked away. He very quickly figured out she was one who couldn’t sit still, which sometimes could be a problem. Her back arched as he licked away, sending waves of pleasure throughout her body. “I-it’s… so strong…” she began to pant.

Cole could still taste the berries from earlier. No way did he want to pull himself free from her snatch. The taste, though small, was so good. Her small body didn’t produce much, but that was okay. Her actions made it so much better for him. She would buck involuntarily against his lips as he ate her out ravenously, making it more enjoyable for them both. To both Cole and Tori’s enjoyment, that awesome moment finally hit her.

With one final thrust against him, Tori’s orgasm hit. Her back arched heavily as a loud moan came from her. He had to let one of her arms go as he pulled his head back and cover her muzzle to quiet her so Sara didn’t come in. Immediately, a paw went to between her legs, shocking him as she rubbed herself during her small orgasm. Letting her other arm go, Cole watched her as she began to masturbate furiously, desperate to ride out the orgasm. “Good job, Tori. Just like that…” he said quietly to her. 

He watched as her chest rose and fell quickly. The small pokémon’s orgasm lasted not long at all where she collapsed in a worn-out heap. “W-what was that?” she asked him as he let her muzzle go.

“That was called an orgasm. When you or someone else touches you down there long enough, you have one and it makes you feel really good,” he explained to her. She slowly sat up and looked between her legs and saw how her fur was slightly damp from how quickly she was rubbing herself. “Did you like that?”

“It felt very good. But why am I wet down there? Is that bad? I’m messy now…” she said.

“No, that’s a very good thing. It made me happy,” he told her. He picked her up in his arms before standing up.

“It did?” she asked.

“Very happy. That means you liked it. I’m happy you did,” he told her. She stayed silent for a moment as he walked to the bathroom. He thought about what he just did and how wrong it was, but how incredibly hot it was. He wanted to do it again, but now he had his eyes on Sara. He wanted her next.

“Did you have one, too?” Tori spoke up finally.

“No, I didn’t. Nobody was touching me, so I didn’t,” he told her. She nodded slowly before humming to herself.

“Do you want one too?” she asked innocently. “I had one and I like to share, so you should have one too! Sara too!”

So much for Sara next…

“Soon, I’ll have one. We’ll do something new, something we’ll both like, okay?” he told her. She looked super interested but nodded excitedly. Soon, the two were in the bathroom where Sara was waiting patiently. “So, who’s ready for bath time?” he asked the two.

“Me!” they both said enthusiastically. He smiled to them as he sat Tori on the ground. He then walked over to the tub and turned it on where the water began flowing into the tub. After turning the water on, he turned to the two.

“So, Sara, Tori is going to go first, okay? She’s not as dirty and has more fur so she’ll take longer to dry. Then we’ll get you going, okay?” he told her. She nodded and walked over to the tub and helped Tori climb into the warm water. Immediately the riolu smiled happily from being in the warm water. 

Without wasting any time, Cole set out on cleaning the riolu. She leaned into his touch, enjoying how his hands worked her body. Since she wasn’t too messy, it didn’t take long or much effort for her to get cleaned. As he cleaned her, she would playfully splash him, where he’d splash back. She would giggle every time, something he enjoyed. She was such a happy pokémon, and he loved that. 

In about fifteen minutes, Tori was finally clean. For someone as clean as her, it sure didn’t take long to get her clean. He enjoyed the feeling of her fur between his fingers. When she was clean, he picked her up from the tub and sat her on a towel laid out on the counter by Sara. She dripped water from her body as she stood there. “Where are more towels?” he asked the smeargle.

“Right here!” she said. He watched as she ran over to the counter and opened the door before pulled out a new towel. Looking under the counter, he saw the girl who owned the two had many towels stacked up and ready to be used. “Mommy knows we need a lot so she always has clean ones for us. Use as many as you need is what she always tells us,” explained Sara.

“Oh well that’s very nice of her. Do you mind handing me one?” he asked her. She nodded happily and reached under and quickly pulled one out then passed it to him. “Thank you,” he said with a smile. She smiled back in response. He took the towel and wrapped it around Tori, rubbing his hands up and down her body to dry her off. 

“Alright, let’s get you in there,” he said, turning to Sara. Before he could react, Sara turned around and ran to the tub. She quickly climbed over the edge and fell in, submerging herself in the water. Immediately after, her head poked up with just her eyes poking over the edge playfully. “Well, that was easy,” he said with a chuckle.

“I like baths!” Sara said, showing the rest of herself. She laid back moments later and relaxed in the water contently. “They’re super fun. And warm!”

“Yes they are,” he said with a smile. He turned back to Tori and used the towel he wrapped around her to help dry off even more. He grabbed it off her body and rubbed her arm up and down. When her arm got somewhat dry, he moved to her next arm, doing the same thing. When her arms were dry, he moved to her legs. Once more, he was eye level with her slit, making it hard to make another move on her.

Cole began to slowly dry her legs off, staring at her entrance as he did. He was pulled from his stare when he felt a paw tab him on the shoulder. He looked up at the riolu curiously. “Do you want to make me feel good again?” she asked him curiously. He closed his eyes and took a deep breath. It was growing increasingly difficult to not do it. “Since I know you like it, you can whenever! I like it too!”

Cole stood up and ignored the offer. He knew it was best, if only for a short time. When he did, he watched her reach between her legs and gently rub her slit. “See?” she said after a moment of rubbing. She showed her paw and that it had that familiar wetness on it. “Will you?” 

Fuck it. I’m done trying. Cole looked over to Sara and saw her still relaxing on her back as she floated in the water. She had her eyes closed, enjoying the quiet. “Sara, we’ll be right back. Don’t go anywhere, okay?” he told her. Her eyes opened slightly before she smiled to him in response. He took that as the okay. He turned back to Tori. “Okay, come on,” he told her. She stood up and held her arms up where he immediately picked her up with the towel still wrapped around.

“So what are we going to do?” she asked him curiously. He walked back to her bedroom and shut the door before walking to the bed. He grabbed the towel from her and sat it on the bed before setting her down next. She climbed backwards with her back against the headboard. She immediately spread her legs for him where he saw her slit waiting enticingly for him. It had the tiniest bit of fluid leaking from it, making him want to dive head-first into her.

The sight alone pushed Cole over the edge. He couldn’t wait any longer. He undid the buckle to his belt and dropped his pants before climbing into bed with her. “What’re you doing?” she asked him curiously once more. Picking her up, Cole scooted onto the towel and pulled her into his lap. 

“Do you remember when you asked if I wanted to feel good?” he asked her. She looked up at him and nodded before looking at his lap. She saw the erection as it rested between her legs. 

“So you want me to make you feel good too? But… I don’t know what to do…” she told him worriedly. “What if-.”

“I’m going to help you. We’ll both feel good. Okay?” he told her. 

“Okay… What do I do?”

“Stand up. I’m going to help you,” he told her. Nodding, Tori stood up and waited for the next instructions. Cole held onto the small pokémon’s waist and lined her up with his member. He felt her squirm slightly when it touched her folds, exciting him. “I want you to trust me. It’ll hurt at first but it’ll feel good soon.”

“Do you promise?” she asked. He nodded quickly.

“I do. Ready?” he asked. 

“Okay…” she responded in an unsure tone. Cole took a deep breath and, in one motion, slid himself in. He only got his head in before he had to stop as he was met with a large amount of resistance. She was much smaller than him so he knew it’d be a fight but he would prevail. “T-that hurts…” she told him. He knew it would and decided to just keep going in hopes it would get better. So he pushed her down harder, sliding in more as time went on. She whined loudly as time went on. “Cole… No more… This doesn’t… feel good…” she kept saying. He ignored her, thinking on only himself. Eventually, he got to the familiar barrier that he expected.

“This will hurt the most. Once it’s done, it’ll be good. Hold onto my hands,” he told her. She whined loudly as she waited for the pain he mentioned. Taking a deep breath, Cole pushed her down harder, forcing himself further in and past her hymen. When it broke, she screamed in pain, making him let go of one side and wrap a hand around her muzzle. 

“Shh… It’s done…” he told her. He rubbed a hand up and down her side, trying to sooth her. He knew she was in a lot of pain, both because of the massive amount of stretching for her little body and from her virginity being taken. As he sat there trying to sooth her, Cole felt a wetness hit his leg. He looked forward and saw tears streaming down her cheeks. ...What… the fuck did I just do… he thought to himself, regretting what he did.

“It hurts… It hurts so bad…” she kept repeating as he let her maw go. 

“I know… I know it does. I’m sorry, I really am. We can stop if you want…” he told her. With her head hung low, she looked between her legs and saw blood trickling down from her entrance.

“Wh… Why am I bleeding? What… What’s going on?”

“That’s normal for the first time, Tori. Do you want to stop?” he asked her worriedly. He knew it’d be hard and painful for her, but she hasn’t outright said to stop.

“N-no… I… I feel…” she stuttered. She rubbed her belly and felt the bulge in her belly. “It’s… It’s… weird. I feel… full. I like it but… it hurts… When will it feel good?” she asked him. “You promised it would…”

“You don’t want to stop?” he asked her cautiously. “It doesn’t hurt too much?”

“No… it does hurt a lot but you told me it would feel good and I like feeling good. So… can… we keep going?” she asked him hopefully.

“Okay, I’ll let you do it.”

“What do I do?” she asked.

“Do this,” he told her. He helped her pull herself up his length then, before pulling free, slid her back down his shaft. She grunted in response but shuttered. “Keep doing this and it’ll feel good soon.”

“Can… C-can you keep doing it until… I get used to it? It… hurts right now…” she asked of him. He was happy to oblige and did asked. He continued to slowly pull her up his length before pushing further back down. He felt her rest her paws on her belly. Due to her size, he could feel her rubbing him through her belly, adding a weird sense of pleasure.

“I can… actually feel your paws…” he grunted. “Keep doing that and I’ll do all the work for us. It’ll help you feel better,” he told her. She looked up to him before nodding. Doing as told, Tori began rubbing her belly slowly in small circles, which shocked her to say it actually did sooth her a tiny bit. For Cole, though, it made him feel extra good as her actions added pleasure to it.

In the beginning, Cole took it slow so he didn’t hurt her too much. Her grunts of pain lasted quite a long time but eventually turned tiny squeaks of pleasure. He had a lot of resistance when he started but her small body soon stretched enough for him to access her easily. Her tiny walls squeezed him harder than he originally imagined they would and made this all worth it. “Do… you remember… t-that good feeling, earlier?”

“Y-yes! I feel it… c-coming…” she told him. 

“Good… K-keep going towards that feeling, o-okay? And I w-want you to p-promise me something, okay?” he told her. “Do y-you promise me t-to not tell anybody? T-this is our little secret,” he told her seriously. He knew that there was a chance she would tell someone and that could get him in trouble. Thankfully, she nodded.

“O-okay! But only i-if we can do this more!” said Tori. He was ecstatic she wanted to do this more with him. If she enjoyed it, then he had a new toy of his own any time we wanted. All he had to do was get permission to watch them more. Then his mind went to Sara. She was his next target and he had to have her. She seemed like a very curious pokémon and that made it easier for him. The possibility was there for him. However, that was something to worry about at a later time.

Right now, he focused entirely on Tori. She squeaked loudly in his embrace with each bounce. Her walls held him tightly, desperate to milk him of everything he had to offer. Her little paws moved frantically across her stomach, drawing him closer to the edge. They were slow in the beginning but the longer it went on, the closer to her orgasm she was. She was shaking heavily against him, her signs of an approaching orgasm.

“C-Cole. It’s… here…” she told him. 

“Good… Don’t fight it, Tori…” he told her. She slowly let her head hang low as he began to thrust harder into her. He wanted to unload in her and knew the second she would cum, he would too. She was so cute and so soft as she rode his member. He wanted her to let loose in his lap, and that was just what was coming. “Be a good girl and give in…”

After one last thrust, that’s just what she did. Her head slung back hard as her back arched. Moments later, her orgasm hit, sending her body into a convulsive state. She shook against his body, riding out her orgasm. Due to her size, only a small amount of her juices came, mixing with the blood on the towel below. “I-I lo-ove this!” she exclaimed happily.

“He-here it comes…” he told her. Her small body’s orgasm didn’t last long. However, she was sent into another shivering state as Cole’s orgasm hit. He slammed her into his lap as far as her tiny body would allow. Holding her in place, he shot rope after rope of his sticky seed deep within her tiny womb. She immediately groaned out loudly from the feeling.

“W-what… is that feeling? It feels… so good!” she told him. He leaned forward and rested his head on hers, riding out the orgasm. Her body immediately took in the tiniest amount of his seed before the rest spilled from inside her. It trailed down her legs and onto the towel, coating it in their love-juices. His orgasm was a good one, but it wasn’t great. However, it definitely felt good enough to hold him over for the time being. 

“D-did you feel good?” he asked her as his orgasm slowly died down. He felt himself slowly softening inside her body, to which she sounded like she was whining to. He rubbed her belly soothingly as he did.

“I felt very good,” she answered quickly. “Can we do that again?” she asked hopefully. He was shocked she wanted to again and, as much as he wanted to, he knew not to. He had to wait or he could really hurt her. 

“Not right now. Maybe later, okay? Don’t forget we’ve also got Sara in the bath still. Plus you need to eat,” he told her. He grunted as he lived her up and pulled her off his limp member. The aftermath of their sex spilled out below them. She shakily stood there and watched him as he cleaned himself off with the towel. “Clean yourself up a little bit with this, okay? When you’re done, go to the kitchen and we’ll eat.”

“Okay,” she told him as she sat down. With himself clean enough, Cole swung his legs over the edge of the bed and stood up. He quickly pulled his pants up and put his belt on. Leaving Tori to clean herself up, Cole walked to the bathroom and saw Sara standing up and watching the doorway curiously.

“Is Tori okay?” she asked immediately when he walked in. She had a worried look on her face as she stood there.

“Yes, she’s fine. Why?” he asked her.

“I had her scream. Did she hurt herself?” asked the smeargle.

“No not at all. Well, a little. We were playing and it hurt her in the beginning but then she felt good after,” he told her. He didn’t want to imply anything but felt he should be somewhat honest with her. He walked over to the tub and got to his knees where he was eye level with the curious and worried pokémon.

“...Played? Played what? Why did it make her feel good?” she asked.

“Don’t worry about it,” she was told.

“But I want to know… I like to play too…” she said with a bit of a pouty face. He rolled his eyes at her and started to help her clean herself.

“If you like, I can show you in a few minutes, okay?”

“Okay!” she responded, perking up almost immediately. She sat down and let him begin washing the paint off her. For the most part, it was easy to do. Some spots were hard to reach but, in the end, it wasn’t too difficult. However, that was until he got past her belly. More specifically, her crotch. He saw traces of paint down there but what seemed really odd to him was a paw print.

“Um… Sara? Why do you have a paw print by your privates?” he asked her. She looked down then up to him.

“Oh. A while ago, I saw a video on Mommy’s phone about another girl touching herself. She made these weird noises as she did but then she got really wet down there and made a mess. She kept saying it felt good and I wanted to try,” explained the smeargle. Cole stopped his cleaning and listened intently. “So I did. Mommy caught me and said not to do that but it felt good to do. Sometimes I do it but then I remember Mommy says not to so I stop…”

“Were you doing that in there?” he asked her seriously. He said he wouldn’t do it again but if she was already exploring herself, then how could he not?

“No… I wasn’t…” she told him. 

“Are you lying to me, Sara? If you weren’t, why do you have paint down there that’s exactly like your paw?” he asked her. He had a plan and it was set in motion. He knew how he could do that for the both of them. 

“...Please don’t tell Mommy… I don’t want to get in trouble… Please…” she told him. He knew he had this exactly where he wanted it.

“I won’t, but you have to do something for me. Will you show me?” he asked her.

“Show you? Show you what?” she asked him curiously. He didn’t say anything and went back to washing her. If he was going to move forward with the idea, he had to wait for Tori to go by. He didn’t want to have her see. So he continued washing her until she finally walked by. When she did, she smiled and waved before running into the kitchen. With her now gone, he decided he could move forward with his plan.

With her being clean enough, Cole grabbed her by the waist and laid her out on a towel he had set out for her. She dripped on the counter as he slowly dried her off. When she stopped dripping, he walked over with her in his arms and leaned against the wall before sliding down to the floor. “What are we doing?” she asked him confusedly and curiously.

He took the towel from around her damp body and rolled it up before setting it behind him. He sat forward and quickly slid his shirt off and sat it on top of the towel. “That stuff your Mommy said not to do, did it make you feel good?”

“Yeah. A lot. Sometimes I got extra wet like the girl in the movies. I like to do it a lot…” she told him.

“Do you want to do that now? I’d like if you let me help you feel good,” he told her. 

“...How?” With her in his arms, he laid her on the floor with her head on his shirt and the towel. 

“Do you trust me?” he asked her. She nodded quickly to him. “Good. I’ll make you feel good but you have to keep trusting me.”

“Do it!” he heard a voice yell out. Cole quickly turned around and saw the familiar riolu standing in the doorway. “He made me feel really good and he’ll do the same for you! I promise!”

“Tori! What did I tell you to do?” he yelled out to her.

“Sorry but I just… I really want to feel good again. I liked how we played and wanted to ask if you’ll do it one more time. Only one more and I won’t ask again today! I swear!” she told him as she stepped forward. He thought for a moment, unsure what to do. He wanted to do this just for Sara but the idea of Tori joining in was too good to pass up. 

“...Fine. Come on, let’s scoot down,” he told Sara. He grabbed the towel from the small stack behind the smeargle and helped her scoot down on the floor. “Tori, sit here,” he told her. He then thought for a moment and shook his head, “Actually no. Let me lay down,” he told her. She nodded and stood up, letting him lay down beneath her. “Okay, now Tori, you are going to explain what to do, okay? Let me see how well you paid attention,” said Cole as he pulled his pants back down, exposing his once-again erect member.

“Oh okay! I can do that! No problemo! But what about-.” 

“Come here,” he told her, waving to her. She walked up to him where he grabbed her around the waist. He helped her step over his face, now straddling his lips with her slit. Without wasting any time, he leaned forward and gave her a lick, making her squeak in response.

“O-oh! Okay! I like that! Okay now Sara, h-here’s what you’re going to do,” she began explaining. 

“Tori, I want you to try and get that extra good feeling as many times as you can, okay? Don’t hold back. Do you hear me?” he told her. She said nothing and continued explaining what to do to the smeargle. She was much bigger so he didn’t think it’d be a problem for her to take his size. He felt her climb in his lap and anticipated the good feeling that was soon to come.

Cole reached up and grabbed Tori by the thighs are pulled her close. Wasting no time, he began licking away at her slit, sending shivers throughout the riolu’s body. She continued to explain and soon began to rock against his tongue as he explained. He was shocked how quickly she began to pick up on the ways to make her feel good and get into it. 

Cole felt Sara grip his member in her paw. She was so much more gentle than Tori and he loved it beyond words. “M-maybe try… pulling it up and down… first…” she said. Doing as told, Sara gently tugged at his member which got a positive response from Cole. He heard the two giggle at him, happy they figured something out on their own. 

“He liked it! Wow!” Sara exclaimed. “But… what about me? I didn’t… I didn’t feel anything good?”

“Yeah, do this now…” she continued explaining. Once again, Cole zoned out as the taste of berries came back. He was in love with the sweetness her insides gave and the way she shivered against each lick. As he did, he felt Sara’s weight grow on top of him as she stood up. He knew what she was doing as she lined herself with him. “Okay, Sara, this will hurt lots but trust me. It’s good after!”

“O-oh… okay…” the smeargle said back. Cole halted his licking and awaited the feeling of being squeezed once more. He heard Sara take a deep breath and slide down him with ease. Because of being much larger than Tori, it was no problem to get him all the way in without a problem. But it confused him - he didn’t get stopped by her hymen.

“Um… Sara…” Cole said, moving his head from Tori’s snatch, “Be honest with me. Have you put things inside you before?”

“...Yeah. One time I did and I think it went too far because it hurt and I started bleeding. But… putting you in me feels very, very good,” she sighed contently. She gently rocked her hips against his crotch, clearly enjoying the fullness inside her.

“...So I’m not the first thing to go in you? Did someone else touch you?” he asked her worriedly.

“Nope. I found one of Mommy’s toys. It buzzed a lot and felt really good to have inside. I kind of want one of my own…” she said with a sigh. Cole smirked. He knew exactly what he was going to do.

“I have one you can have on one condition,” he told her.

“Wait, really?! I can have one!? Okay!”

“Only if you make me feel extra good. And you have to promise me no more touching yourself unless I’m around, okay? No more when it’s Mommy home. Deal?” he told her.

“...But what if I feel like I need to? Sometimes I really want to and it hurts if I don’t…” she told him. He was confused but then remembered this was the age where she starts to really explore her body, so it didn’t surprise him she got the urges to masturbate.

“...Okay, but you be sure she isn’t around. Do it at night when everyone is asleep, okay? If you do that, I’ll get you one but I have to keep it with me,” he told her. 

“Deal! How do I make you feel extra good?” she asked.

“That’s easy! Just lift your butt up and slide down. That’s it and you’ll feel good too! But wait, did you not feel hurt when you first put it in?” Tori asked curiously.

“Nope, not at all. But it felt really good!” Sara answered enthusiastically. The more these two talked, the more he was shocked how they were. Neither had a problem with what he was doing to them and wanted more. There had to be a way to keep coming back for them. Hell, he even considered buying them off the girl, but that was something to worry about later. For now, sex was important. “S-so… like this?” she asked.

Sara pulled herself up before sliding down. She wasn’t slow at all but that was fine with him. He didn’t mind a quicky in the slightest. “Good! Maybe even try to go fast! He might like that!” Tori told her.

You little mind reader… he thought to himself. Sara nodded in response and quickly pulled herself up before sliding back down quickly. Each time she did, she would grunt in response, showing her own enjoyment. 

“So what about me?” Tori then said, wiggling her butt against Cole. 

Fuck these two are so fucking perfect… he thought to himself. Once more, he pulled her close and began lapping at her slit. She sighed contently and leaned into his licks, letting him do as he pleased. She gently rocked her hips against him, getting the extra bit of pleasure she could. 

“S-sometime… we s-should swap places! You might l-like him licking you!” Tori said loudly. However, Sara said nothing as she was already bouncing rapidly in his lap. Her walls squeezed him tighter than Tori’s did, almost not letting her move. Had she not been using all her strength, there was probably no way she’d have even been able to move. “I-I already… feel really good…” she said.

He had barely even been licking her folds and could feel her orgasm approaching. Perhaps it was because she was just now getting into the idea of sex and liked how good it felt so she was extra sensitive, but she sure didn’t ever last long. That was fine with him, though. That just meant more for him. “A-already!” Tori yelled out. He felt her lay down on his chest with her legs wrapping around his head as her body shook heavily. Her juices came more than before, coating his tongue entirely. However, it was very quickly over with.

“Mmmm…” Cole moaned contently as Sara bounced in his lap. She had a paw between her legs that ran along the length of him that didn’t fit. From how it felt, she probably had it against her clit as well as she bounced, wanting to feel good like her sister was. 

“T-this is… so fun…” Sara grunted happily. Her tail wrapped around his leg, using it to hold herself up. Her walls squeezed him tightly as more slipped in. He could feel she was substantially wetter than the riolu, which was fine with him. It made her actions much easier to do. She also seemed much more into taking him than Tori did. 

As she bounced, Cole wanted to see how Tori would react if he could find her g-spot. So he pushed his tongue in and was met with the tiny bit of his own semen from their previous time together. She sighed loudly and relaxed against his actions, letting him probe deeper. “I-I-I like this s-so much more…” Tori panted. That only solidified what he thought. He searched endlessly for that particular spot and, because of her size, it took no size to find. He dragged his tongue over it and it made her buck hard against him. “W-woah! W-what did you do? Do it again!” she demanded.

Cole was happy to oblige. He continued to drag his tongue over that special spot she had, sending the little riolu in a frenzy. He felt her tongue resting against his belly as he continued, no doubt putting her into a state of bliss. “T-that’s so good! Keep going!” she kept telling him. He had no problem and no desire to stop. He was way into the taste of her.

“C-Cole… I think… that feeling is here…” Sara told him. 

“Good! T-that’s super okay! Let the feeling happen and you’ll love it!” Tori said between pants. He heard Sara moan out loud and didn’t need to be told to let it happen because her motions stopped suddenly as her orgasm hit her hard. She slammed herself down against his crotch and sat there, convulsing heavily against him. Her juices actually splashed in a large amount below them, coating his crotch and inner thighs. “T-this is s-so, s-so much better!” she yelled out loudly.

Cole groaned as her insides desperately milked him for his seed, but nothing ever came. He was close… very, very close. Instead, Tori’s second orgasm hit just as Sara’s did. This one was much more powerful as she grabbed onto his sides tightly and pushed her butt against his face harder than ever before where her juices came out in a ferocity that would match Sara’s. The taste of berries and her butt being forced against him was enough to finally get him over the top.

Cole groaned loudly as his orgasm hit for the second time. His own body shook harder than ever before as his member erupted deep within the smeargle. He felt his sticky seed coating her insides, causing the smeargle to groan out loudly about how warm it was and how she wanted it all to herself. For someone her age, she sure seemed into the idea of being taken.

Tori was the first to die down from her orgasm. She, being the most tired from three very quick orgasms, rolled off his belly and to the floor. She shakily stood up and looked over to Sara who had her hung low. Cole got a good look at her and saw how heavy she was panting and made him smirk. She was so worn out. “H-how was it? Do you feel good now?” asked Tori.

“I-I loved it… Will we do this again?” she asked hopefully.

“Whenever you two want when Mommy isn’t here. For now, let’s get you two some food, okay?” he told them. They both nodded and Torri stepped back, giving Cole the space to sit up. When he did, he gently rubbed Sara on the cheek who leaned into the petting. After a moment of that, he gripped her side and pulled her free where virtually nothing came from the inside of her. She really took his load without a problem. She was a good one to be with, that’s for sure.

Standing up, Cole quickly wiped himself clean and then wiped up the mess they all made. As he did, he thought on what he just did with them both. He wanted to say it was bad but they were at the age where it wasn’t abnormal for them to be taken. Plus, Sara’s hymen was already broken so it wasn’t even that bad. Plus, they really enjoyed it! So, was it really that wrong? He didn’t think so, and they wanted to keep going. So in the end, he thought it wasn’t bad.

When they got cleaned up, Cole emptied the tub and led them into the kitchen. The two small pokémon yawned tiredly as they waited for him to cook their food. He reached into his pocket and pulled out his phone and saw it was starting to get a bit late. It was also getting to be their bed time, just as the lady told him. “Alright girls, let’s get you filled up and into bed.”

“Will you come back again?” they asked him.

“Do you want me to?” he asked them as he warmed up their dinner.

“Yes! We really liked playing and want to again. So, will you?” Tori asked him. He thought for a moment. He knew if he came back again, whenever that would be, he’d be doing this more. They wanted him to, so why not?

“If you both want me to, sure. I’d be happy to play again,” he told them both. They smiled brightly and went about eating their food when it was set out. In no time, they were both full and their plates were empty. Again, they both yawned and tiredly as he quickly washed them off. He saw how droopy-eyed they were. He chuckled and picked them both up and carried them to their room. Walking to their bed, he sat them down on it and reached for the towel. He expected a mess there but it was clean. There was only one way. “...Tori? Why is this clean? I thought it had a mess?”

She looked up at him tiredly and blushed slightly. “Well like… I did clean myself but then I smelled it and it smelled so good. I ended up just… licking whatever was on it and I liked the taste…” she explained. Cole went wide-eyed at her but laughed. 

“You are one brave girl. Before bed, we’re going to do one more thing,” he told them both. They both looked up curiously as he pulled out his phone. He squatted down and looked them both in the eyes. “Remember how good we felt? Remember how you touch yourself when you want to feel good?” he asked Sara. She nodded as he stood up. “Sometimes, I like to look at pictures of girls who’re cute to help me. Will you let me take a picture of you both to if I want to feel good?” he asked.

“Okay!” they both said quickly. He smiled at them. “What do we do?” Cole positioned them so Sara was on her back with her legs spread widely. He then had Tori climb on top, giving him a view of their beautiful slits and soft butts. “Like this?” 

“Perfect…” he answered as he snapped a picture. “One more. Both sit up and spread your legs…” he told them. They quickly did as asked and smiled as they did. He had his own little girls who were happy to do anything for him. Taking the second picture, he pocketed his phone right after. “Thank you girls. Come on, let’s get you all tucked in,” he told them.

The two climbed into bed and beneath the blankets. Tori laid further away so he leaned over and kissed her on the head. He couldn’t control himself as he reached beneath the blanket and gently ran his finger along her slit, making her shiver. Who knew when he’d be able to again, so he had to one last time. “Remember what I said?” he asked her as continued to stroke her. She nodded in confirmation. “Good... Sleep good,” he told the smeargle.

He then turned to Tori and did the same thing. However, she saw it coming and the second his hand went beneath the blanket and to her slit, she grabbed his hand and held it there. “One more for me?” she asked, almost begging. He sighed and tried to fight it back. He knew he couldn’t.

“No more. However, if you two want, you can help each other. You two are sisters after all. If the other wants, ask and you might get help,” he told them. The two looked to each other before nodding. They scooted closer where he backed away. He saw the blanket move slightly down low and he thought he knew why but decided to not probe. The two pokémon closed their eyes and he backed up. Turning the light off, he closed the door until it was cracked. “God this day was fucking awesome…” he mumbled to himself.

He walked to the kitchen and just before sitting down, heard the sound of a lock being opened. He looked down a hallway and saw the lady who hired him walking in. She looked exhausted but smiled when she saw him. “Oh, hi Cole. How was everything? Were they good?” she asked as she sat her purse down.

“They were perfect angels. We had a ton of fun playing together today. They even said they want me to come back and play some time,” he said with a chuckle. He saw her smile but if only she knew what that meant.

“Well, that’s good. My job has me working weird hours for a while so I’ll be needing your help more often. Maybe we can set up some kind of permanent babysitting service?” she asked him hopefully. In his mind, Cole was screaming at the idea. It was like he hit the jackpot.

“Sure, I’d be happy to watch them again,” he said calmly. The girl smiled and nodded. 

“That’s great news. Mind if we discuss that real quick?” she asked. He nodded and followed the lady to the table. The two talked for a bit and it was set that he’d be needed at very random times. If he wanted them at his house, they were welcome and it was almost encouraged as he had more they could ‘play with’. Again, only he knew what that meant. Regardless, he was excited.

This was all too good to be true.


	2. Chapter 2

Over the next week, Cole continued watching Sara and Tori. The three had a lot of fun with each other, not wasting a beat in helping the other feel good. Throughout the week, Tori and Sara had become quite a bit more tolerant of his size and even began to beg him to play with them in that way. He loved he had gotten them to that way and fully accepted what he had become. They begged him for it and not once did he make them do anything if they didn’t want to. That wasn’t to say they even hinted at not wanting to. No, they really liked to come onto him, both literally and figuratively, so it was more him helping them… not that he would complain.

A week after meeting Sara and Tori, Cole got a call to babysit a new pair of pokémon. He asked about them and found out they were actually younger friends of Sara and Tori. Rory and Anne were their names. He was advised that Rory was a bit of a troublemaker and was that way so she had attention on her while Anne was the more relaxed one. She didn’t like being in trouble and often times actually cleaned up whatever Rory had messed up so she wouldn’t get in trouble. It was sweet, but he could see that as a problem.

As much as he hated it, the first thing his mind went to was if he’d be able to get with these two like he was with Tori and Sara. However, when he found out they were actually younger, he threw that idea to the side. Tori and Sara were young enough, so for him to go even younger felt incredibly wrong to do. He knew it was wrong and knew that if he did want to, which he did if he were to be honest, he’d need to wait until they were a little bit older. It was hard to even give Tori and Sara the attention they wanted because of how small they were, so for the two new pokémon to get it would be virtually impossible.

Cole was never given the species of the two pokémon. All he was told was their personalities and their names and that the four pokémon were friends. He also learned from the trainer of Rory and Anne that the two looked up to Tori and Sara. Apparently they all liked to play together whenever a babysitter wasn’t needed. Cole sure hoped the two kept their promise to keep things between them a secret.

The last thing he needed was two more to worry about.

After a full day of watching, and lots of “playing” with Tori and Sara, Rory and Anne were dropped off. His eyes immediately went to the small pokémon’s bodies. “That’s Rory,” their trainer, a guy in his upper twenties, told him. She was a small quadruped that was blue and black in color. She had a bright, yellow star at the end of her tail. He then pointed to the other one. “And that’s Anne,” he then said. Anne was brown and stood on two legs. She had a bright, white belly with long claws.

“Sandshrew and shinx. Interesting combination of pokémon. Plan on battling?” Cole asked the guy.

“Rory! Anne!” a small voice yelled out. Cole instantly recognized it as Tori’s, who came running toward the group. The two pokémon perked up at the sound of her voice. “Come on! Mommy’s going to be here soon so let’s play while we can! Sara also wanted to tell you something super, super important!”

“Okay! Come on, Anne!” Rory told her sister. The sandshrew nodded and ran alongside the other two pokémon where Sara stood on the opposite side of the room. When they all got together, they hugged in a cute way. Cole couldn’t help but stare at the two new pokémon. His mind very quickly became flooded with lewd thoughts of the two, which he tried his best to shake off.

“Not going to tell the nice guy hello?” their trainer spoke up. They said nothing as they continued to talk amongst each other. 

“Don’t worry about it. I’ll get to know them later,” Cole said with a smile. The guy nodded in response. “So, what can you tell me about them so I don’t worry or any rules to set?” Cole asked. Since they were in Cole’s home this time, Cole invited him to the table to sit down and talk, which he did.

The two talked for quite a while, Cole having to periodically eye the group of pokémon. It made him uneasy how Tori and Sara kept pointing at him like he wasn’t going to notice. However, he did every time. When he’d call out and ask why they’re pointing, they’d all just giggle at him and not answer. He had a feeling he knew what about but prayed he was wrong.

After almost a half hour of talking with the new guy, Tori and Sara's trainer came and picked them up. Just before they left, the two pokémon jumped up in his lap and kissed his cheeks affectionately. Right as they jumped down, they both “accidently” stepped on a certain spot in his lap before turning to eye him playfully. They knew full well what they were doing and knew they’d get “punished” for it by him later. The two loved it just as much as he did.

When Tori and Sara left with the trainer, Rory and Anne’s trainer said good-bye to them and told them to be good to Cole. “We will! We’ll play a lot, right Mr. Cole?” Rory asked him. “Tori and Sara said he’s a lot of fun to play with so we’ll have fun.”

“I’m glad. You’ve got my number. Let me know if you need anything. Bed at a normal time, yada yada,” the guy said. Cole nodded, knowing the basics of it. This wasn’t the first time he’d be watching someone younger so he knew what to do and all of that. With that and final hug from their trainer, the guy left, leaving just the three of them. “So, wanna tell me what you two were talking about earlier?” he asked the two curiously.

“Tori and Sara said you were a fun babysitter is all. You three played… special games together. They said that, whatever it was, was something that made your body feel good and to tell you we wanted to try. So can we play like that?” Rory asked him hopefully. He sighed to himself, hating the fact that he was right.

“No, you’re too young. They shouldn’t have said anything to you about that at all. Maybe when you’re older I’ll show you,” he told the two in a serious tone. The looked down dejectedly but nodded. He felt bad because he didn’t doubt that the other two bragged about the fun they had and that Cole would do it with them too, but they were too young. However, like before, he doubted that this would be the end of it. “Come on, let’s find you two something to do. What do you like to do?”

“Sara was teaching us to paint!” Anne told him quickly. Cole smiled to the two.

“Well good news for you is I have a ton of paint. Come on, I’ll show you,” he told the two pokémon. They nodded happily and followed him into another room of the house. With nobody living with him, Cole had room to turn one of the bedrooms into a small kids room since he’d be babysitting. It was filled with things younger pokémon could do like easels and paint, a small toy chest, blocks, the whole nine yards of toys. 

Almost immediately, the shinx and sandshrew ran over to the easels and sat patiently. They didn’t rush him or anything like Sara and Tori, and for that he was grateful. He took his time in setting out the things they’d need like the paint itself and brushes. One thing he very quickly learned was to have old rags nearby for when messes happened. Of course, rags were used for other things with the three of them, but that was personal.

When everything was set out for them, the two small pokémon began painting. To say that Tori and Sara were messy would be an understatement. While messy, Rory and Anne were much more enthusiastic about it. Since they were young, he wanted to try and teach them a few things like spelling, even if it was only a few minor words. The two seemed really interested in being taught by him, and that was something he liked. Of course, being so young meant they had a shorter attention span. He wasn’t surprised so when they started doodling, he let them without interrupting.

For a while, the two continued painting by themselves. Cole didn’t need to keep a direct eye on them the entire time so he went to his phone. Throughout the week with the smeargle and riolu, he snapped many, many pictures for himself to enjoy. They were of the two pokémon in so many positions, ranging from solo pictures to lesbian acts. Without a doubt, if he got caught with these, he’d be in a lot of trouble.

Without question, Cole’s favorite picture was one he got today of the two. Tori laid on her back with her paws forcing Sara’s head between her legs. Her legs were hiked up high as she had the most orgasmic look on her face he’d ever seen. Her tongue lolled out with a tiny bit of her saliva trailing free. As she was eaten out, Sara used her tail to gently pull her lips apart, giving Cole an inviting view. Her juices trickled from within onto the towel below, leaving a mess for him specifically.

Without a doubt, Cole felt lucky beyond words. He had so many pictures like that that it was unreal. It amazed him that every time he watched them was different. You’d think they’d only be able to do so many different positions, but that was wrong. It was always new as the two were eager to feel good. He was always more than happy to oblige to the two, ready to make them feel as good as they wanted. It was fun because they’d go until they would fall asleep and just after waking up, they’d want more.

“Mr. Cole?” Rory spoke up. He felt her patting at his leg. He looked down at the shinx as he was pulled from the pictures. 

“What is it Rory?” he asked her. He saw one of her paws held up high to him that was covered in paint. He then looked beyond her and saw the lid to one of the jars was on the floor. He then sighed. “Why did you dip your paw in it?” he asked her as he got up and walked over to the paint. Thankfully, Anne hadn’t done the same and kept painting.

“Well I got bored. Sara told me if I was you’d help me not be bored. You know, she said to keep asking about that special playing. Can we please do that? I want to know too…” she begged him. He sighed once more and shook his head.

“No, Rory. I said when you’re a little older I will. Don’t ask me again, okay?” he told her in a stern voice. She huffed at him as he reached for her paw. He was shocked when she pulled away from him and rolled onto her back.

“Yeah well… Sara told me a way to make you play,” she said. He was confused until she spread her legs wide for him, giving him a very nice view of her privates. She looked up at him expectantly. “She said when she lays like this, you always touch her. So, touch me now,” she demanded him.

“Rory, stop,” he told her, trying to resist the urge. “Sit up and let me clean your paw. I’m not touching you down there. It’s inappropriate to-.”

“No! She told me if you wouldn’t, to do this.” Cole was about to ask what she meant until she used her paint-covered paw to cover her thighs and slit with the paint. She frantically rubbed until he grabbed her paw, making her stop.

“Excuse you, young lady. What did I just say?” he asked her in a serious and stern voice.

“Now you have to! I want to feel good, so touch me!” she yelled once more. Cole was very quickly picking up on how the little shinx was going to be. He was warned about her being a little troublemaker but he wasn’t ready for this. “Play with me!”

“You’re going to be one of those, huh…” he mumbled to himself. He got up and grabbed one of the rags that were by the easels. When he sat down again, he pulled Rory into his lap and sat her down. He then gently ran the rag along her inner thighs, trying his best to avoid her slit. However, there was no way he’d be able to. She painted every bit of her privates, making him have to touch her. “Just don’t think anything of it…” he mumbled.

Cole took the rag and wrapped it around his finger but dabbing it with his tongue to get it wet. He then began to gently scrub the still-wet paint off her body. He played it smart and started with her paw. It took nothing to clean her paw, where he then moved to her belly. He saw her smirking like she had won and it bugged him. However, he pushed on and worked on cleaning the paint from her. She stayed relatively motionless until it came close to her slit.

As he inched closer to it, it reminded his first time with Sara when he cleaned her. She had her legs spread willingly for him and the curiosity grew in him. Just… one touch and he’d be good. Those same thoughts came to him as he looked down at Rory. That playful smirk, the way she was inviting and practically begging for his touch… How could he not go through with it? Just… just one time and he’d be okay.

Cole unwrapped his finger from the paint-covered rag and rested a finger just above her slit. Both he and Rory locked eyes as the two were both beyond curious of the other. What was he going to do to her to make her feel good down there? How would she react whenever he would slide his finger inside her? The two wanted to find out more than anything in the world. “...Please, Mr. Cole?” she spoke up.

Cole was immediately brought back from his thoughts. He looked down and saw his finger just barely above her slit. His crotch was clean, yet he didn’t remember cleaning there specifically. Cole pulled his hand back, fighting the urge to give her what she wanted. “N-no, you’re clean. Don’t do that again, hear me?” he told her. Once more she had a dejected look but nodded. She rolled and stood up before looking back at him. She thought for a moment before taking a step forward.

“...Just one? I want to know what it feels like… just a little… Please…” she begged as she lowered her front end with her back raised. “Tori… told me you liked when she did this so maybe if I-.”

“No! Stop asking me!” he yelled at her. She recoiled from how he yelled, immediately making him feel bad. He didn’t mean to yell but he was serious. “You’re too young to do that, Rory. I’ll tell you what. I promise when you’re as old as they are, I’ll show you. Is that a deal?” he asked her. She looked down at the ground before up to him.

“...Pinky promise?” she asked. He smiled and held his pinky up to her where she wrapped her tail around it. She very quickly smiled at him.

“Yes, as long as you pinky promise no more trouble. Now go keep your sister busy for a few minutes while I do something,” he told her. She nodded to him and ran back over to Anne. The two began talking amongst themselves once more where Cole opened his phone again. He immediately went back to the pictures of Tori and Sara. However… he began imagining someone else in the positions. 

With each lewd picture, he’d imagine Rory in one of the spots of the girls. Her butt in the air for him, her pussy dripping wet because of him, her legs spread with another girl having their head between them… every scenario he imagined putting her in was absolutely perfect. He wanted to pair her up with one, or both, of them and teach her all what she wanted to know. She’d have a lot of fun getting put in her place. Very quickly she would learn to listen and, if she didn’t, they’d start all over.

“Rory! Stop!” Cole heard Anne yell out. He looked up from his phone and saw Rory dipping a paw in the paint once again. “Nice job, now we’re in trouble!” she yelled again.

“No, you’re not…” he told Anne. The two looked over to him and saw the irritation on his face. “What did I just tell you, Rory? Why aren’t you listening?”

“I am! I’m keeping her busy! She likes to clean so I made a mess! Tell him!” Rory said to Anne, hoping to be backed up.

“But not on purpose! Daddy said to be good…” she told her sister.

“Come on, let me clean your paw again…” he told her as he sat his phone down, not even bothering to close the pictures. Rory huffed in response as she walked over. She then held the paw out to him and allowed him to clean it. When it was done, she looked past his legs and saw his phone.

“What are those pictures of?” she asked curiously. Cole went to grab the phone but she quickly jumped over him and pushed it towards Anne. “Secrets aren’t nice!” 

“Anne, give me it back,” he told the sandshrew. She picked it up as Rory ran over but looked at the picture.

“...Why are Tori and Sara… touching each other there?” she asked innocently. She used a claw to slide the picture over, no doubt showing a new one.

“Is that what feels good?” Rory asked him as she looked up. She saw Cole had quickly closed the gap between them and reached for the phone. However, Rory grabbed it with her maw and jumped over him in one quick action.

“Rory! I’m not playing games,” he told her in an annoyed tone. She smirked at him in response as she jumped up on the bed in the room. She sat the phone down and continued scrolling through the pictures. “Give it to me. Now,” he demanded. She looked up from the phone then at him.

“Why is it bad for you to touch me like that? They both look happy and I want to be happy! I’ll give it back, pinky promise, but I want to feel like they do!” she said with a smile. 

“No. Give it to me. Last time I’ll tell you.”

“Rory stop! Daddy’s going to be mad at us…” Anne said worriedly. Cole looked down at her reassuringly.

“No, you’re being a good girl, Anne. Thank you,” he said with a smile. She still had a worried look but nodded. “Rory on the other hand…”

“Tori and Sara said that what you two do is a secret. Well, Daddy tells us secrets are bad. Maybe Daddy would show me how to feel good if I showed him these-.”

“Anne,” Cole interrupted the shinx. He was annoyed but he was done. She just crossed a line. 

“Y-yes, Mr. Cole?”

“I want you to do me a favor. I want you to go outside and wait for a few minutes. Rory and I need to have a private talk, okay?” he asked her in a gentle tone. He didn’t want to show annoyance and, thankfully, he suspected he didn’t. She nodded and stood up before slowly waddling out of the room. “Please shut it too!” he called out. 

“Yes, sir,” she said before shutting the door behind her. Once it was, he turned to Rory who had a smirk on her face.

“If you won’t, Daddy will because Daddy loves me and-.”

“Be quiet,” he told her as he stood up. She did as told and watched him walk over to him. Rory quickly picked up on him being mad at her. He picked her up before climbing into bed with her.

“...Are you mad at me, Mr. Cole? I didn’t-.”

“Yes I am,” he interrupted. “I told you many times to stop and listen but you won’t. You really want to see what it feels like when they do that stuff?” he asked her seriously. Rory nodded enthusiastically in response. “Fine. I’ll gladly show you then,” he told her. Cole grabbed Rory and sat her next to him before quickly undoing his pants. He slid them down and presented him to her. “See that?” he asked her, motioning to his privates. She nodded curiously and eyed it.

“Y-yeah?”

“Lick it. If you want to do what they are, then you need to make sure it’s covered in your spit. Otherwise, it’ll hurt for you a lot,” he told her. She looked up at him in an unsure way.

“B-but they aren’t…”

“Oh yes they are,” he told her. He grabbed his phone from next to Rory and pulled up a specific picture. It was of the two between his legs as they looked up at the camera. Tori held his member his in her paws as Sara licked away at it. He then showed it to Rory. “See? They do it, so can you. If you want to be a big girl like them, then you do it too.” 

“I-I didn’t know that they did that! I just wanted you to make me feel good…” she said in her defense. He shrugged, hardly caring at all.

“And I told you when you were older. But you wouldn’t listen to what I was saying so now we’re doing it differently. You had chances. So either we do it this way or never,” he told her point-blank.

“But you promised!” she yelled back at him. “You pinky swore!” 

“And you pinky promised you wouldn’t get in any more trouble today. You didn’t do that. So it’s either now or never. If you listen now and do as I tell you, maybe I won’t tell your Daddy how much of a bad girl you’ve been with all the not listening…” he told her. Her expression quickly went to worry at the mention of her Daddy yelling at her for misbehaving.

“No! Please! I promise no more trouble! I swear!” said Rory in a scared tone. He smirked, glad to have control back.

“Then do as I say. Do you want to feel good like them?” he asked her once more. She looked up at him momentarily before nodding. “Then lick that and make sure it’s nice and wet. Understand me?”

“O-okay…” Cole saw the young pokémon was nervous and confused but she kept saying she wanted it. He had no plans to but if she wants to act this way for not getting it, then fine. He’d stoop to her level and give her exactly what she wanted. There were plenty of other ways he could have gone about punishing her but he didn’t care. No, he wanted to send her a message that he is in charge and not her. 

The small shinx slowly leaned in and sniffed at his member. She only did once or twice before doing as she was told. Her tiny tongue dragged on his skin, making him sigh quietly. She did it again before pulling away from him. She looked up at him as she spoke, “D-do I have to do this? I… I don’t like how it feels…”

“Yes, you do. You said you wanted to do what they do so now you are. Do you want them to know you were a chicken and not brave like them?” he asked her. Her demeanor changed almost instantly. She was once unsure but now she held a brave and confident look. He smirked at himself, knowing just how to get to her.

“No! I can do it like them! Promise!” she told him. She stood up and crawled between his legs and sat down once more. She huffed before leaning in once more. Again her tongue licked his skin, adding just the tiniest bit of saliva to it. Cole could immediately tell she was inexperienced but that was, by no means, a shock to him. If he could mess with her and talk her into anything by saying she was chicken, then he knew he got a good one. “Like this?” she asked him as she kept licking.

“Perfect. Remember, keep doing that and make sure it’s all nice and wet. When it is, I’ll show you what kind of fun we have, deal?” he told her. She gave an affirmative nod to him.

“Deal! Tori and Sara aren’t the only big girls! I’ll show you!” she said. Wanting to move it along, Cole brought a hand to the shinx’s head and rested it on top before pushing her closer. She growled with a determined tone to show she was no baby like he jokingly said and that she was a big girl like the other two. 

Rory quickly picked up her licking. She didn’t like the feeling of when his member throbbed slightly against her tongue but she pushed on. Cole was amazed at how quickly she changed when he said that. At first, her licks were slow but they very quickly picked up. He figured she must really not like to give oral so she just wanted to get it over with. That was fine with him. Each time she started to pull her head away to start back at the base, her furred lips would gently brush against the base of his shaft, adding a tiny bit of enjoyment to her licks.

Soon, his entire shaft was covered in her saliva. He let go of her head where Rory pulled away with a proud smile. “See! I told you I could! Now what?” she asked him curiously. Picking her up, Cole sat the shinx in his lap right on top of his member. It twitched when it brushed against her butt, making her make a surprised noise. He quickly brought a hand down to her belly and rested his finger just above her slit.

“We’re going to see how tight of a fit this will be. You’re very small and I don’t want to hurt you. Now it’s my turn to make you feel a little good,” he told her. She seemed super excited about the idea of him making her feel good. She leaned back into his chest when he used his arm to spread her legs wide for him. “Relax and let me do this. It’s very, very important you stay relaxed, okay?”

“Yes! What’re you going to do?” she asked him. Cole stayed silent and didn’t answer. Instead, he used his pointer finger to slowly drag from the bottom of her tiny slit to the top. He immediately felt the shinx jump from the surprised contact. She knew he was going to touch her there but she didn’t expect it to actually feel that nice. He did it again, getting the same response. “I-is this what you do the whole time to feel good?” she asked him. Again, he ignored her question. This was a serious thing he was focusing on. While he did want to actually put her in her place, he wouldn’t if she wouldn’t be able to take him. There was no way he would hurt her severely.

After a few more strokes, Cole brought the same finger up and stuck it in his mouth to lube it up with his spit. She looked up curiously at him and watched him. He could faintly taste something, but he didn’t know what. When he pulled his finger free and back to her slit, she spoke up loudly, “W-wait! Don’t put your spit in there! That’s icky!” she yelled.

“So you don’t want to feel good then?” he asked her.

“N-no! I do! But spit is icky and-.”

“Then relax,” he told her. Before she could do anything, Cole gently pushed his finger in. Rory inhaled sharply from the feeling of something stretching her cub insides. Her legs straightened out from the pleasure. No doubt was this something she enjoyed a lot already. He got to the first knuckle before he had to stop and let her adjust. “How does it feel? Do you-.”

“M-more!” she yelled at him. Cole was surprised to hear her sound so demanding. 

“But does it hurt?” he asked her cautiously. It may have felt good but he didn’t want to go too far for her first time.

“...A little but it feels a lot better than hurts! So, keep going! Remember, I’m a big girl and big girls can ignore pain!” she told him confidently. Cole liked that mindset. So he pushed on further, his finger sliding in to the second knuckle. Her back arched as more of him slid in. He could feel her tail wagging madly against his belly from how excited she was to feel so good. This time, instead of stopping at the second knuckle, he pushed further, soon his entire finger stuffed inside her virgin body. “I-I see why they said to ask you to play like this! My body feels so, so good and it feels extra good down there. B-but… it kind of hurts now… C-can we not put m-more in please?”

“We won’t, Rory. Don’t worry,” he told her. She nodded with a smile and took a deep breath. Her walls squeezed his finger tightly from the foreign object. No doubt was her body far from ready to be penetrated but he didn’t care. She enjoyed it and that’s what was important. He thought about how his length wouldn’t be a problem. What did worry him was his girth. Would it be too much for her? There was only one way to find out. Slowly, he pulled his finger out, Rory groaning as he did. 

“W-wait! I liked it in there! Why did you take it away? I did what-.”

“Because I’m putting something else there so I also feel good,” he told her. She was confused until she remembered what she had been licking moments ago.

“...Will it hurt?” she asked him worriedly.

“It probably will in the beginning. But you tell me when to stop. If it hurts too much, you tell me right away and we’ll stop and do something else. I mean it. You promise me you will,” he told her. She nodded to him as she looked up at him for comfort. He gently pat her head to calm her. He knew for a fact it would hurt, and a lot most likely, but if he could get all of him in, she would like it. He knew that from experience.

Even with that in mind, he did worry about her yelling from pain. He looked around and saw the tiny rag he used to wipe up the paint earlier. He grabbed it and rolled it up before holding it in front of her. “Bite down onto this. We have to be quiet. If you’re going to be loud, then this is needed. Okay?” he told her. She hesitated before nodding. Leaning forward, she took the rag in her mouth. “Ready?” he asked her.

“Mmhm…” she said scaredly. 

“You’re a big girl. Remember what I said, okay?” he told her. With one last nod from her, Cole picked up the small pokémon and hovered her over his member. After lining himself up with her slit, he slowly pushed her downwards where she took the head in. It took a bit of pushing but it fit, though only barely. He heard her groan in pain but not much. “You okay?” he asked her. He heard her breathing heavily but nodded slowly. “Do you want me to give you a minute to get used to it?”

“Mm-mm…” she answered, shaking her head no. With a deep breath, Cole pushed her down a tiny bit more. This time, a much louder groan came from her. He had to hold her paws down as he felt her trying to push free from his grip. He knew that she was stretching more than she was ready for and the pained groans and whimpering was evidence of that. He got only a fourth of his length in before stopping once more.

“Do you want me to stop?” he asked her. She continued breathing heavy and nodded her head. “Do something else?” he then asked. She stayed motionless for a minute, the whimpering never stopping. Eventually, she shook her head no. He let her paws go where she rested them on his hand. She leaned her head forward as well, using it to rest. Eventually, she nodded once more to him. “Continue? Are you sure?” he asked her. Again, she nodded. “Okay… but Rory, you need to know this next part is going to hurt… a lot. Are you sure?” he asked.

“...Mhm…” she told him. Cole sighed worriedly. Maybe it was best he actually didn’t. This was going to hurt her a lot and he knew that. Was it worth it to him? Doing this to her? He could do other things with her that would make her feel good. He felt her paw on his hand gently rubbed it. He looked down at her and saw her expression demanding him to do it. 

“...Okay… I’m sorry for how much it’ll hurt…” he told her. She nodded and leaned her head on his hand once more. The two took a deep breath and pressed on. She groaned out in pain as more of him slid in. However, he came to the spot that signified a girls virginity. He didn’t stop at it, though. He pushed himself right past her hymen where her groans of pain turned into muffled screams of agony. He hushed her and stopped the second he got past and gently rubbed her back with his hand.

On his hand he felt wetness coming from her. No doubt was the pain too much for her. He looked down lower and saw blood coming from between them. Her body was shaking like mad from the pain and he wished he could do something to soothe her, but he couldn’t. All he could do is wait. “You’re doing good. I promise it’ll feel good soon…” he told her. Her tears kept flowing, as did he words of promise.

For minutes, the two sat and waited. Cole was not going to rush this. He would continue when she was ready, if she wanted. After another few minutes, she spit the rag out from her mouth. “I-it hurts… so badly…” she whimpered loudly.

“I know it does, but the hardest part is done. I promise from here on out, it’ll feel good, okay?” he told her.

“O-okay…” she sniffled. Cole brought his hand up from her back and to her cheeks, wiping away the tears.

“You know what the best part about this is?” he asked her. He knew just the way to get her mind off the pain, even if it was only a little.

“W-what?”

“You get to tell Sara and Tori how much of a big girl you are now. Only big girls get to do this, and that’s what you are, right?” he told her. Though it was very, very small, he did see her smile. “Isn’t that right?”

“Yeah…”

“What? I can’t hear you…” he told her. Her frown was slowly changing to a smile. This time, she nodded very slowly.

“You’re right… I’m a big girl, just l-like I told you…” she said to him. 

“That’s right, you are,” he said, rubbing the top of her head. She leaned into the rubbing, the faintest of purrs coming from within her. She lifted her head from his arm and looked down low.

“W-why is my belly like that?” she asked. He looked over her and saw her belly was bulging slightly. “Is that bad?”

“It shouldn’t be. That’s like that because I’m inside you and you’re so small. If you watch, you’ll be able to see it moving whenever you’re ready,” he explained to her. 

“...Will it really feel good? I… I’m scared it won’t…” she told him truthfully.

“I swear it will. Pinky promise even,” he told her. She took a deep breath and nodded.

“Okay… make me feel good please… Just… no more inside me than that. It hurts too much…” she begged him. He nodded to her, respecting her boundaries. Cole leaned back against the headboard of the bed and placed both hands beneath her butt. He pulled her up before sliding back down. Rory whimpered as he built up his speed. “I-it doesn’t… feel good yet… just hurts lots…”

“Just hold on, Rory. Soon,” he told her. Cole hoped it really would feel good for her. He didn’t want her to be one of those who actually didn’t feel pleasure during sex. While it may not be enjoyable for her, it really was for him. Rory was miles tighter than Tori and Sara ever were. He could barely fit inside her and, had she been any smaller, he knew it would have been impossible. Her walls were incredibly tight, almost to the point it was painful for him as well. But he pushed on, just for her.

Soon, Cole had a steady rhythm as she bounced in his lap. Her pained whimpers slowly died out and were replaced with pleasured squeaks. Her eyes were once shut but were now intently watching her belly expand and contract. “I-it… does feel… kind of good now…” she said with a pant. He smiled, happy he was right.

“I told you it would. You just enjoy it, okay? You’ll feel even better soon…” he told her. Her eyes were fixated on her belly, never looking away.

I-it… keeps getting bigger… and smaller…” she said in awe. “I feel… really good down there…” she said. “D-do… you feel good… too?” she asked him. “I hope so…”

“I feel very, very good,” he told her. He really did feel good from how tight she was. It was incredible how good he felt. The way her small, furred body rubbed against his belly made it even better. He could feel her insides stretching for him to accommodate his massive size. Well, in reality he was average but for someone as small as her, he was huge. It was truly amazing he even fit in her to begin with.

As she continued bouncing his grip, Rory’s head began to lean back against his chest, the pleasure taking over. “I-it… doesn’t really… h-hurt anymore. Just… lots of feeling good… I-I don’t want to stop feeling good!” she told him. Cole chuckled at her and nodded. He was happy she wanted to now be one he could… play with. Having three cubs of his own to use whenever he wanted was something he never thought he’d want, but now he did. 

Cole closed his eyes and let the pleasure take over. Rory kept babbling on about random things that were happening, not that it shocked him. This was a new experience for her and everything interested her young mind. To enjoy it the best he could, he tuned her out, letting the pleasure wrack his brain. He loved how her insides squeezed him and very quickly accepted him. Because of how tight she was, Cole knew he’d be done with her much quicker than any of the other girls.

Rory picked up on him being quiet, so she too stopped talking. When she did, she closed her eyes like Cole and very quickly realized that it felt a lot better for her when she focused on the feeling of him inside of her. Each thrust from him sent a huge wave of pleasure throughout her small body and she loved every second of it. She didn’t know it, but her young body was approaching her first, and most definitely not last, orgasm.

“I-I feel… really… tingly down there… is that bad?” she asked him between pants. Cole was grunting, struggling to get his words out to her.

“N-no… Relax and focus on that. That’s the really good feeling. Remember… no being loud, okay? If… you need the rag, t-tell me…” he told her. She nodded to him in response, focusing on what that feeling was. It made her muscles tense and feel so much better when she did focus on it. She felt her outsides becoming more and more damp the closer she was to orgasm.

Cole found it harder and harder to fight back the orgasm. She was so, so tight and her body felt like it was craving his seed. Her little whimpers and squeaks made it virtually impossible to fight. He wanted to fill her full of his cum and he knew she wanted it too. His breathing was becoming shallow and sporadic, his sign of an orgasm approaching. “R-ready to feel… super good?” he asked her.

“Y-yes!” she yelled out. Just as she answered, Cole’s body and mind erupted in a sea of pleasure. He stopped forcing her up and down on his shaft as he held her as far down as she was able to go. Seconds later, a massive load of his seed spilled from deep within him, quickly filling the shinx up. She groaned loudly as his seed couldn’t sit inside her. Due to her size, it spilled out below the two, coating the sheets below them.

Right after his orgasm, Rory’s hit. She squirmed like mad in his grip. She shook so much that it required him holding her around the midsection to keep her still. “I-I feel s-s-so good! Thank you, M-Mr. Cole!” she continued yelling out. “I-I promise I’ll b-be good from n-now on!” Cole ignored her but wished she actually stayed quiet. But it was too late as her own juices came rolling down his member. It wasn’t much but every vibration from her shaking definitely showed him much she enjoyed it.

The two rode out their orgasms together. Compared to Rory, Cole’s was very short. When his died down, hers continued going. Her body shook for a long time, against him, no doubt not used to this much pleasure and euphoria. He was happy though that she enjoyed it so much. “H-how was it? Do you feel good?” he asked her.

“I feel so, so full. W-what is that warm stuff inside of me?” she asked him as she looked up. She had the absolute biggest blush on her muzzle from how good she felt.

“It’s called semen. It’s how you have babies. When a male-.”

“I’m gonna have a baby?!” she yelled in disbelief. Cole laughed at her.

“No, Rory. It’s impossible for me to get you pregnant and have a kid. But if a male pokémon and you did what we just did, you would,” he explained to her.

“O-oh… phew! I didn’t want a baby!” she giggled. 

“You’re much too young anyways. But did you enjoy it?”

“Lots! I promise I’ll listen to you from now on, Mr. Cole. No more bad girl for me! Only big girl!” she said with a happy smile. “Can we… do that again, though? Since I know how good it feels, I want to do it more!” 

“R-Rory? A-are you okay?” a quiet voice spoke up. Cole and Rory looked towards the door of the bedroom and saw Anne’s head poking in. She had a concerned look on her face as she stepped in further. “I-I heard screaming and I got worried. I thought he was hurting you for being bad…”

“No! He made me feel good, just like Tori and Sara! Mr. Cole! Will you show her?” Rory asked him hopefully. He watched as the sandshrew stepped closer to the bed before jumping up.

“H-he did? But… I thought you were going to be in trouble… Promise you didn’t hurt her?” Anne asked Cole. He nodded to her.

“I promise, Anne. I would never hurt any of you, even if being bad,” he told her. She nodded and looked to Rory. She was curious about was going on.

“So… um… How did he um… make you feel good?” she asked her sister. “Your belly is huge! Can I… poke it?” she asked her sister with an intrigued stare. “Will it hurt?”

“I don’t know if it will! Go ahead!” she told the sandshrew. She nodded and leaned forward being gently poking her sister in the belly. Rory giggled in response. Through her small frame, Cole could barely feel the sandshrew’s paw touching him. “That tickled!”

“What… is that stuff coming you? ...Why is part of him inside of you?!” she asked worriedly. 

“Mr. Cole, will you please show her how to feel good? Instead of me having a second turn, I want to give my turn to her!” she said. Cole couldn’t help but smirk.

“I don’t know. Tori and Sara kind of tired me out. You only made it worse. I don’t know if I could for her or not…” he told her truthfully. She thought for a moment before nodding. Cole gently lifted her up and off of his softening member. More of their mixture spilled below, soaking the bed even more.

“B-but you used you finger! Remember? Maybe you could do that? Please?” Rory kept asking. “...You want to know what it’s like to feel good too, right?” she asked, turning to the sandshrew. Anne looked unsure as she fiddled with her small claws.

“...Maybe… I don’t know… All three of you have felt good and played with him and I kind of want to… You all three said it feels good so I would like to as well… yes, I do,” she mumbled quietly. Cole sighed to himself. He was incredibly tired because, like he told Rory, he was very tired. “Can we play Mr. Cole? If not it's okay…“

“Please? It'll make me sad if I did and won't be allowed to…” Rory told him. Come sighed to himself. He really didn't want to but he didn't want to look like he was playing favorites between the two. If anything, Anne had sort of earned her right to. 

“I don't know. I just…” he mumbled to them. The two Pokémon looked down sadly and it made him feel bad. He looked at Anne and thought for a moment. Though she was small, she quite a bit bigger than Rory was. He wouldn't have to worry about hurting her. “...Okay, fine. You've been a very good girl since you got here and even tried to keep Rory from getting into trouble. I think you've earned a reward,” Cole told her. The sandshrew looked up at him excitedly. 

“R-really?”

“Yep. When you're good, you get rewards. When you're bad, you get… punished. Both can be fun depending on what you like,” he said. Neither picked up on what he meant so that would have to be something he'd teach them, especially Rory. 

“Well… What do I need to do?” Anne asked him curiously. 

“Rory, you lay down for a few minutes and behave. Don't do anything or say anything until I give you permission. Understand me?” he instructed the tiny shinx. She nodded but looked like she had a question. 

“Umm… What… if I start to feel weird? Like… if I want to be touched?” she asked him. “You're going to be touching her…”

“You have paws, don't you? You can touch yourself. That is a very good thing to do if you feel like you want to be touched because somebody won't always be around,” Cole explained to her. “There will also be days where I'm not with you to help. So you'll have to do it yourself. Maybe I'll teach you both to help the other,” he told them. The two seemed excited about that idea before nodding. Rory took a few steps away before laying down on her side. Cole reached forward and grabbed Anne and pulled her close to him. “I want you to relax. Remember, this is a reward. Tell me if you want to stop.”

“O-okay… I will…” she nodded. Cole could tell she was incredibly nervous and knew he would need to work her into it. She was going to be a delicate one and that was okay with him. It was a challenge for him and challenges were always fun. At the same time, he had to show her he'd respect her boundaries, should they ever come up. He didn't want her first time to be bad because that would send her a lasting impression. If she didn't enjoy it this time, no doubt would she not want to do it anymore. 

“Remember… Relax…” he told her gently. She took a deep breath and did as told. He could feel her physically relaxing which he was glad about. That showed she trusted him. With her slowing relaxing, Cole began. He trailed his hands up and down her shoulders, hoping to release the tension she felt. From his shoulders he moved to her bell, gently rubbing it. She sighed lightly from the contact. Inch by inch he trailed further down. 

Cole eventually came to the sandshrew’s slit. Wasting no time, he dragged a finger along the length, awaiting a reaction as he did. She whimpered quietly from the contact. He couldn't tell if it was a good one or a nervous one. So he dragged his finger against her folds again. Again, a whimper came out. With his left arm, Cole held her against him. Almost immediately Anne brought her paws up and rested them on his arms. He felt each time she was touched down lower, he claws would poke into his arm. It was a sign of enjoyment in his eyes. So he wanted to press further and see what he could get her to do. 

“Anne?” he spoke up. 

“Yes Mr. Cole?” she answered him. Cole brought up his finger he'd been using to touch her and held it close to her mouth. 

“I want you to do something. For me to be able to make you feel good like I did Rory, my finger needs to be wet. I want you to put it in your mouth and make sure it's covered in your spit. Lick it, suck on it, however you want to. After that, you will feel very, very good,” he told her. Cole saw she was very unsure of it but decided to trust him. He had done this with the others and she knew he'd promise to make her feel good. 

Anne leaned forward and didn’t waste time in licking his finger. He was very shocked at how eager she seemed after the second lick. One of her small paws were used to hold his hand still as she leaned in closer. Her licks were turned into gentle suckles as she engulfed the finger in her mouth. Cole’s eyes were wide as she bobbed her head slightly along the length of his finger. She was fluid and rhythmic, almost as if she had done this before or watched someone do it. There was no way it was either of them, yet it seemed to come to her naturally.

“I-is that good, Mr. Cole?” Anne spoke up. Cole was brought from his amazed stupor when she spoke up. She held his hand with a slight blush on her face as she looked up to him. He nodded and pulled his hand from her grip and gently pushed her to lean back against his chest. 

“Very good. One day, we’re gonna do something different with your mouth. For now, lean back,” he told her. She was curious but Cole noted the excitement she seemed to have. She had no problem leaning back for him to work. 

“S-so what’re you gonna do?” she asked him curiously. For someone as shy as her, Anne seemed really eager to move on. It was fun to think about how each of them were so different but so similar.

“Gonna see how much resistance I have,” he informed her as he brought his hand down between her legs. Her gaze followed his hand lower and lower where it stopped just at her slit. Anne stayed silent and watched and waited. Gently, he trailed his saliva-soaked finger along the length of her slit. Anne didn’t give much of a reaction to the touch besides a slightly eager jump when he touched her. He repeated the action a few more times, hardly getting anything from her once again. “Hmm… so you’re not into that…” he mumbled. 

Taking it further, Cole rested his finger in the middle of her slit before pushing it in. This time, she gave a surprised squeak in response. Her legs immediately tried to close around his hand but he was quicker. He held her legs open with his free hand before shoving his finger in deeper. She reacted positively to him going deeper, even more so than Rory did. “T-that feels r-really good!” she yelled out as she looked up to him.

“That’s good. Try to relax. You’ll keep feeling good,” he told her. She tried, but it was hard for her to relax from the way she felt. When he got as deep as he could, he began to pull his finger free, the sandshrew reacting negatively to it. Her hips involuntarily tried to follow how he pulled to keep it in, but he was stronger and held her in place before quickly sliding back in. Again, she squeaked in response. “Well, guess you’ll really enjoy this then…” he told her.

“W-what?” she asked him. Again, she looked up at him and he saw the bigger blush she had. She looked back down and saw the tiniest bit of juices on the bed below her. “I-is that normal?” 

“Very,” he answered her. Cole pulled his finger out from her slit quickly so she couldn’t fight back. She whined in response from feeling that emptiness. Cole picked her up and scooted off the bed. “Okay, I want you to lay on your back with your feet off the bed. This’ll be best for you. You’re a lot bigger in size than Rory so I don’t think you’ll have a problem with this, maybe even enjoy it more.” 

“O-okay,” she said. Anne did as she was told and scooted over just a tiny bit so her legs slightly off the bed. Because of hows he was built, there wasn’t much room for her legs to dangle. Instead, they stood straight in the air. However, her size made it so he could perfectly see her large, glistening slit. It was incredibly inviting and he couldn’t wait to feel himself inside of her. Like he said, she was much larger than Rory because of her species, so her taking him shouldn’t be a problem.

Cole scooted himself over and stood up. The height of the bed required him to stand, or at least crouch, to be able to slide himself in her. If anything, a little repositioning would be all that’s needed. He eyed her and thought for a moment. “Actually, Anne, this won’t work for me. Roll over and put your butt up. You’re a bit smaller than I realized,” he told her. She was confused but rolled over for him and put her butt in the air. It made the position and angle much easier for him now. “Perfect…”

“A-am I o-okay, Mr. Cole?” she asked him nervously. She wanted to be good for him and was worried she wouldn’t be. 

“Perfect. You look great, Anne. There’s a lot of things I want to do right now but this will be the best…” he told her. She smiled happily at his words and nodded. Scooting closer, Cole gripped his erect member and used it to gently rub against her slit. The sandshrew whimpered nervously but instinctively pushed back slightly. Even at such a young age, she has the instincts to mate when presented the chance. He liked that. “Ready?”

“Y-yes… Is it… gonna hurt?”

“It hurt me a lot,” Rory spoke up, “but it felt good not long after! Big sister will be here the whole time! Promise!” she told her. Anne looked over to her as Rory scooted closer and nuzzled her head into her sister. With the question answered, Cole pushed on. He slowly pushed himself against her slit, sliding his length in her inch by inch. As much as he hated to say it, she was not as tight as any of the girls. She was tight, no doubt, but not like the others. She also didn’t seem to really mind the feeling of him inside of her. She reacted positively, but not like he expected. Anne hardly showed any signs of discomfort as well.

“It… It doesn’t hurt much…” she said. 

“Does it feel good?” he asked her as he stopped about halfway in. From how he was, he guessed he could probably fit about another quarter of his length without problem.

“Umm… yes… a little bit. Not like when you touched me with your finger though. It’s… umm… a little big…” she answered him nervously. “I-is that bad?”

“No, not at all. Do you not want me to do it?” Cole asked. She remained silent for a moment. Anne gently wiggled her butt before speaking up. 

“No… I do. Maybe you’ll help me like it. Go ahead, Mr. Cole. I trust you!” she told him in a confident voice. He admired how she trusted him so much and wanted her to enjoy it. So he pushed on. When he got in as far as he could, he began to pull away before sliding back in just a tiny bit further. He repeated himself, slowly building a pace. “I-it… feels a little good…”

“Good… That’s very good…” he told her. She nodded and sighed, letting him take over her body. He liked that she submitted so easily and became his little toy. She was obedient and very quick to make sure he did what he wanted, even if she didn’t seem to enjoy it too much. That wasn’t to say she wasn’t enjoying it, because as he built up his speed, tiny, almost inaudible grunts came from the little one. She enjoyed it, but not as much as she expected.

For Cole though, he was quickly getting into it. She wasn’t tight, but she was taking him better than any of the others. He was able to fit more which made less need for extreme tightness. With Anne, it was a snug fit - not too tight and not too loose. It was like her small, frail body was meant for him. He insides held him perfectly, as if they were meant to do nothing but that. But even with all that, he didn’t like that she didn’t enjoy it as much as him.

However, Anne said she was enjoying it as he built up speed. Maybe she’d enjoy it enough soon. He looked forward and saw her head resting on her tiny paws, even louder squeaks coming from her as he got faster with his thrusts. She seemed to not really enjoy when things were slow and sweet, rather she enjoyed when it was fast and to the point. He could accept that. If he wanted a quickie, he’d go to her.

“I-I l-like how f-fast you’re going… Mr. C-Cole…” she said between whimpers. He liked that. So he kept up his pace, enjoying the quick sex he’d get. With quickies, he knew he wouldn’t last long. The faster he got, the more her insides held him tightly. She definitely liked it quick, and that was becoming more and more evident. “I-it feels s-so good n-now…”

“Good… Just keep… enjoying it…” he told her. She said nothing but whimpered in response. Cole reached forward and rested a hand on her head and gently pushed her down further. She shivered when he did, confirming his suspicions. She liked to be used by him however he wanted. He could be rough and she wouldn’t mind. Just to be sure, he let her head go and grabbed both of her paws and held them out in front of her. He then spoke up, “Do you like when I push you down? When I’m a bit rough with you?”

“Y-yes, I-I really do… I… don’t… know why. It’s… not nice to be r-rough but I l-like it…” she huffed to him. He smirked and nodded before pushing her head back down into the bed.

“Good. Don’t you move. You lay there and enjoy it like a good girl should,” he told her. It was weird but he felt her shiver as he told her what to do. She definitely was a submissive one and one who had no problem doing what was told of her. Perhaps that was why she took everything so serious when told what to do and what not to do. She just… enjoyed it. 

“Y-yes, Mr. Co-.”

“No speaking,” he told her. She shivered once more and quieted up. The more he bossed her, the more she melted beneath him. Each thrust had power and speed in it, helping her enjoy it just as much as he did. She wanted fast, she got fast. It wasn’t taking much for him to come closer and closer to the edge. The grip she held on him wasn’t what was helping him along. No, it was how she submitted so quickly and easily. The power he had over her small, young body drove him mad.

As he thrusted harder and faster into her, her whimpers picked up quite a bit. Her small, rough form was pressed roughly into the mattress below them as if she was nothing but a toy to him. She was obviously much more than that to him, but that’s how she seemed to enjoy being treated. She wanted to be used and wanted whoever was using her to be rough. He was more than happy to oblige.

“Aren’t… you hurting her?” Rory spoke up worriedly. He grunted as he looked up at her. He didn’t like that she was interrupting her sisters turn but knew it was only because she was worried. She was watching with a nervous expression, not wanting Cole to hurt her. 

“Not at… all…” he grunted as he continued his thrusting. 

“He’s… m-making me f-feel so g-good!” Anne yelled out. Rory continued looking her over but slowly nodded.

“...Promise he isn’t hurting you?” Rory asked her sister. The sandshrew nodded ecstatically in response.

“...Do you think we can play again after?” she asked Cole soon after. The shinx looked up from her sister and into Cole’s eyes. She seemed to be thinking for a moment turning to her sister. Like Anne, Rory lowered her front half and showed her butt to him. “I’ve been a good girl and really want to… Watching Anne feel good makes me feel… weird.”

Every time Cole thought things couldn’t get better, they did. He had a cute, little pokémon begging for him to fuck her and he was more than ready and willing. But not yet, he wanted her to wait. This was her sisters turn. However, the sight was something he didn’t want to forget. “Go get me my… phone…” he grunted to Rory. She looked up slowly before nodding. The shinx quickly got his phone and handed it to him. “Back… down like you were… but in front of Anne...” 

Cole halted his thrusting as she positioned herself like she was just seconds ago. She had a slightly pained face and it made him wonder if it’s because she was really into being touched. If that was the case, there could be a lot of things that he could get her to do just to get her to feel good. However, she’d work for it, that much was for sure. So many ideas ran through his head that it excited him. He’d have to sit down one day and jot them down for later.

He opened the camera app on his phone and positioned it so he could get both Rory and Anne in the picture, while also showing he was deep in her. It was a bit difficult but he got it. This was already one of his favorites because it showed both of them ready and willing to be taken by him. He closed the app and tossed the phone to the side. “You’ll get your turn when we’re done…” he told Rory, not wasting any time in going right back to where he was with Anne. She immediately let out a loud groan from the suddenness of the pleasure. 

Cole knew exactly what he wanted to do with her and Anne. He wanted to do so much but one thing in particular fit them perfectly and when he was done with Anne, he’d be more than willing to give them both what they wanted. “M-Mr. Cole…”

“What is it?” he spoke up to her. Once more, he pushed her down roughly into the sheets below, the sandshrew whimpering out of joy. Man, she loves to feel force and powerless… she’s… different… Cole thought. 

“I-I… I feel…” she panted heavily, unable to finish her sentence. He knew exactly what that meant and was ready for it. With each thrust, Cole felt himself growing closer and closer to the edge. He couldn’t wait to fill up her small body with his seed and claim her as his own. Just a few more thrusts and she’d be his and only his…

“Good?” he asked her. He put on an obviously fake but aggressive tone to his voice. She whimpered loudly again but nodded. 

“V-very… I-I don’t know w-what’s coming soon b-but…”

“You let that good feeling take over, do you hear me? You relax and let me do the work. You better not fight it or we’ll do this all over again…” he told her. She gave a final whimper in response, signalling she understood. Truthfully, he didn’t mind the idea of her wanting to keep going. Regardless of what she did, they weren’t done. No, they were far from it. They’d get a small break before they got back into it. He hoped this would go on for quite a while before their owners came to pick them up.

Anne’s insides squeezed Cole tighter than they had since they began. They quivered like mad as she inched closer and closer to her orgasm. Had he not been overpowering her like he was, she’d be squirming all over. But that bit of resistance from her made it even better because he got to power over her. With the other three, it was just them submitting and him using them. Her? It was like a playful struggle and he loved it. It gave her a bit of difference between them.

Cole found it almost impossible to hold it in any longer. He thought he’d hold it out until she came but he physically couldn’t anymore. Something came over him, whether it was his enjoyment of her struggling or something else, but he couldn’t hold back his pleasure any longer. After one last, very rough thrust, Cole pushed himself deeper than he had with her, catching her off-guard. She whimpered loudly from the sudden pain of being stretched but then let out a loud, much louder than before, moan of pleasure as his seed erupted within her.

Cole’s body shook above her as he let loose a torrent of his seed. Much to his surprise, she took it much better than any of the others. Her body warmly and happily welcomed every bit he had to offer to her. The feeling of her walls rhythmically squeezing him of his essence made it so, so much better for him. The only thing to send him into an almost euphoric state was when her orgasm hit right after.

For such a small pokémon, a huge amount of juices came pouring from her insides, splashing against his crotch and the bed below him. Anne whimpered and moaned happily below him, the feeling of her first orgasm overpowering her tiny mind. Cole felt good, but nowhere near like she did. “That’s it… Be a good little girl and let it out for me…” he whispered to her. “Only good girls get to feel that good…”

Anne continued her tiny whimpers for quite a while after her orgasm began to die down. Cole had grown used to the orgasms and how quickly they faded so it didn’t take him too long for him to grow limp within her. He quickly pulled himself out where a mixture of their juices spilled out between them. He grumbled to himself for not putting a towel down to catch the mess. That was just unnecessary laundry he had to do now. Oh well… Might as well keep dirtying it…

As Anne laid in a tired heap, Cole climbed back into the bed and rested his back against the headboard once again. “Alright you two. You want to keep going, right?” he asked them. Rory nodded excitedly she’d finally get to again and awaited instructions. Anne slowly nodded soon after as she looked up to him. However, the idea would have to wait as Cole’s phone began to ring loudly, making Cole grumble irritably in response. “Seriously… Anne, give me that please.”

Anne got up to her feet and grabbed his phone before stumbling over to him. She collapsed in his arms soon after and began nuzzling into him. He took the phone from her and saw it was their owner. “Well fuck,” he mumbled. “Girls, remember what we do stays quiet and a secret. You promise me right now.”

“We do but we want to play more!” they said simultaneously. 

“We will play a lot more after this call.”

“Promise?” Rory asked.

“Promise,” he smiled to her. He then clicked the answer button, “Hey, what’s up?”

“Hey Cole! How’re the girls doing?” he asked him.

“Rory and I had a little trouble in the beginning but she’s been a good girl since we talked. She was just nervous around me I guess but we worked out a way to make sure she doesn’t. Anne has been a perfect little angel as well,” he explained to him. The two pokémon smiled happily at how they were described by him. 

“Oh? How’d you get Rory to stay out of trouble?” he asked him.

“Just had to keep her busy with… games is all,” he answered in a way only the three of them knew. 

“I see. Well I’m glad they’ve been good. So I’m just gonna let you know I’ll be leaving her soon. Got free quicker than expected,” explained the man. Cole’s heart sank. He immediately sat up and eyed the two of them. They were a mess and he’d need to clean them.

“O-oh! Okay! When will you be here?” Cole asked worriedly.

“Half an hour? Fourty-five minutes max,” he answered. 

“O-oh! Okay! That’s fine! I’ll see you then!” Cole said. The guy said the same thing back before hanging up. “Well, fuck. Girls, sorry, but we can’t do anything more. Your trainer is on his way here and we need to get you two clean before he gets here. If he finds out what we did, we’ll all be in a lot of trouble,” he told them in a serious tone. However, neither were having it.

“But you just promised! You said we would keep playing!” Rory told him. He nodded and picked them up quickly.

“I know I did, and I’m sorry I’m not keeping that promise. Next time we’re together, we’ll play all you two want, deal?” he offered them. The two looked to each other before trying once more. It was like they were on the same wavelength because the two of them quickly rolled onto their backs with their legs spread wide open for him. 

“Not even if we’re fast? Pretty please? We’ll be good girls just for you!” Rory told him hopefully. It was like inner demons were fighting inside him for how she said that. 

“I’m sorry,” he told them both as he quickly scooped them up. The two huffed sadly that he wasn’t going to keep his promise. 

“Mr. Cole…” Anne spoke up. He tried to ignore her because he knew she was going to start begging. The trio entered the bathroom where Cole sat them in the tub. “Please… one more? It hurts down there since you touched me and when you did, it felt better. Just… one more quick… please? I don’t wanna go home and hurt until we play again…”

Cole grumbled to himself. He told himself no more but he didn’t find it fair to them. Being so young and after experiencing your first orgasm always made you want more and when you couldn’t get them, it did hurt. He knew if he sent them home like this, there’d be a chance he’d get found out. He couldn’t risk that. But they were still unexperienced so they’d take longer than he had to be sated… unless…

“Fine, a quick one. Last one then we’re getting you clean. Okay?” the two nodded, agreeing to his offer. In a flash, he got up and headed to his own bedroom. He rummaged through one of his drawers and pulled out two things he’d planned on using on the other girls first but felt these two needed it more now than they did. Being brand new and unused, he had to undo the packaging and, not long after, returned with the two items. The two pokémon eyed them curiously.

“What are those?” they asked.

“These,” he held them up to them as he got eye level with the two pokémon, “are two toys used for making you feel good. One is called a dildo and the other is a vibrator. The dildo,” he held up the bright pink, penis-shaped toy, “goes inside of you while the vibrator doesn’t. Both do vibrate though, so no matter who gets what, you’ll both have quick orgasms and that’s a promise. Now, who wants-.”

“I want that one,” Anne interrupted as she pointed to the dildo. He was in no place to argue, but did want to know if that was okay with Rory. She seemed a bit dejected but nodded. 

“Alright. Remember, quick. Come out of the tub,” he told the two. The two small pokémon did as told where he picked them up one by one and sat them on the counter. He picked up the small dildo and used his own spit as a lubricant, though he doubted he’d need it from how much he just filled up the sandshrew. However, he wanted to be safe than sorry. When it was all lubed up, he gently rested the tip of the dildo against her slit. “Ready?”

“Yes I am, Mr. Cole!” she answered him. Just as he did in the bedroom, he pushed roughly into her where she sighed contently. It didn’t take long for the full length of it to be embedded within her. “That feels so, so good, Mr. Cole…”

“Well just you wait. It gets better,” he smirked at her. She looked back curiously at him. Cole gently pushed her backwards so she laid down. She didn’t resist him at all. When she was laying down, he pressed the tiny, black button on the dildo where it whirred to life with a subtle buzz. Her back arched from the sudden, intense feeling of the toy vibrating in her, touching her insides in ways she hadn’t even expected. 

“O-oh! I l-like this l-lots!” she yelled loudly. He smirked, happy she did. He then turned to Rory who looked on with eager, curious anticipation. He then held up the vibrating toy for her. 

“Alright. You turn around, butt up. I think you’ll like this a lot,” he told her. She did so without any need to be told twice. Like the dildo, Cole flicked a switch on the toy where it immediately came to life, a much louder buzzing coming from the toy. Just from how the toy moved, he could tell this one would be much more intense than the other, but the other was more meant to be filling and just add a little more. This was supposed to be super quick. 

“Ready!” she yelled excitedly. With a nod, Cole leaned in closer and held her hips with one hand before resting the loud toy against her folds. Almost immediately, the small feline bucked her hips lightly from the sensation. A surprised gasp came from her soon after. When she got used to it, Rory began to push back against the toy, wanting to feel it as much as she could. “T-this feels s-so much b-better…”

“I’m glad you like it,” he told her with a smile. He was glad this was enough for the two of them because there was no way he could physically go another round, not after everything that day. Plus, he loved to be able to sit back and watch the girls pleasure themselves. It gave him time to relax. “Here Rory,” he said as he pulled the toy away. She whimpered before turning back to him with pleading eyes. He then positioned the handle of the toy so she could hold it with the main vibrating part resting against the top of her slit where her tiny clit was. “You hold it and do what you want.”

Without hesitation, she grabbed the two with her paws and pushed it onto the counter before literally sitting on top of it. Cole watched as she began to involuntarily grind on the toy, quickly coating it in her juices. It vibrated loudly as it rested on the counter but he cared none. Watching her gently grind from being unable to sit still was probably one of the hottest things he’d ever seen. He knew that he’d love watching them share it next time they were able…

He then turned back to Anne. she quickly figured out she was able to use the dildo to masturbate with by pulling it out and pushing it back in. Using both her paws, the sandshrew was toying herself roughly as her legs were spread widely. He noted how her eyes were shut tightly, no doubt still somewhat on the orgasmic high from earlier. Very quickly the counter was becoming wet with both of their juices.

“That’s so good Mr. Cole…” Anne whispered quietly. He couldn’t stop watching as she continued plunging the dildo within her, all the while whispering about him. “I’ll be a good girl, promise… Make me feel good…” she kept saying. The way she whispered about him in such a way really got to him. He wanted to rip that dildo out of her paws and just go to town on her again. But he restrained himself from it, opting to just keep watching. Then an idea hit him.

He quickly ran from the bathroom and his room before grabbing his phone. When he got back, he sat on the tubs edge across from the girls and once more opened his camera. However, instead of taking a picture, he began recording what was going on. Why he never thought to actually record his time with any of the girls was beyond him. 

As much as he loved hearing Anne talk about being his little girl and the likes, he found himself focusing on Rory much more. Out of the two of them, he noticed that she was the one who got a lot more wet a lot more easily, and he loved that. The puddle beneath her was growing rapidly as she continued grinding on the toy. Stepping closer, Cole gently picked her butt up from the toy where she whimpered slightly from being denied. “Shh…” he said quietly.

“Please let me finish… I’m… so close again, Mr. Cole…” 

“M-me too… Mr. Cole…” Anne said. Cole positioned the phone so he could see between her crotch and the toy, where a strand of the shinx’s juices connected the two. He reached forward with two finger and gently dragged them along the vibrating part before rubbing his fingers together and showing the camera. 

“On your back,” he told her as he told up. Rory immediately rolled over as he handed her the toy once again where she pushed it against her folds. Her position was awkward but gave him the view he wanted for the video. “Anne, next to Rory,” he told her. Her eyes shot open at the sound of his voice. In the blink of an eye, she was sitting next to the shinx where the two leaned into each other for support, both desperate for their release once more. “Good girls. Remember who helps you feel good. Anytime you want to do this, you are allowed to come over. I’ll be waiting for you…”

The sound of his words seemed to be enough for the girls to finally be pushed over. Rory was the first to hit her final orgasm. The amount of force she used to push the vibrator against her was great enough that, had her slit been a bit bigger, would have probably slid into her. Who knew what that would have caused; he assumed good things though. He focused on the shinx as her body shook harder than ever before. “I-I love t-this toy!” she yelled out loudly. 

Rory slowly topped over onto her side as she continued rubbing the toy against her clit. Beneath her was a large puddle of her juices that continued getting soaked up in her fur as she began to involuntarily buck against the toy. He knew if he didn’t get it now, he wouldn’t ever get it back. So he reached forward and gripped the toy from her where she looked up at him. She looked like she wanted to protest but simply laid her head back down on the counter tiredly. “That’s a super good girl, Rory. I’m proud of you for that.” He then clicked the button off and sat it down next to her.

“Thank you, Mr… Cole… That toy was… lots of fun. I promise I’ll be your… little girl forever now…” she told him. He smiled at her before turning to Anne next. With the camera in one hand, Cole gently pushed Anne’s paws off the vibrating dildo before gripping it himself. Before she could react, he rapidly and roughly plunged it within her. She put her paws on the counter below her, using it to hold herself up.

“Th-that’s perfect M-Mr. Cole! I love b-being your little girl!” she said happily. Everytime the two said that, it drove him even more mad. The sight of her folds graciously accepting the toy was such a beautiful sight. Anne had her head hung low as she bit her lip while her orgasm hit. She huffed loudly as more of her juices quite literally sprayed like mad. He could tell that this orgasm was far more better for her than the one he gave just by how she acted. More than likely, it was because the vibrator was hitting spots better than he could.

While her body shook, Anne reached forward and held Cole’s hand still as the toy was embedded deep within her. “P-please… don’t take… it yet… It hurts… when you move like that now...” she told him. He nodded, knowing it was because she was becoming sensitive from the vibrations. However, he had to get it out now. So he turned it off where she began huffing tiredly. After a few moments, she gave him the okay to take it by removing her paws. He then quickly pulled it free from her.

“Not done, girls… Just one more thing…” he told them. The two looked at him both tiredly and curiously. They seemed interested in doing whatever which made him happy. Cole then motioned for Rory to stand up, “Anne, stay where you are. Rory, stand over your sister,” he said. She was confused but nodded. After a few shaky steps, Rory stood over her. “Okay, gently lay on her. Right here,” he told her. Rory looked back as he helped her rest her slit against her sisters. “Good girls…” he said as he backed up. 

Cole took a moment to enjoy the view of their wet butts and slits resting on the other. Rory was dripping wet on top of her sister and it took every bit of willpower to not lean in and lick them both clean. Any other time he would have. But with the lack of time he had, he couldn’t. So with the best footage he could have possibly asked for and a picture that’ll last a lifetime, he put his phone down and picked up the girls then sat them in the tub. “You two did great. How’re you feeling?” he asked them.

“I feel so, so good… And sleepy!” Anne told him. He chuckled and nodded as he stood up. He took an already dirty towel and sat it on top of the mess the two made. 

“My body is all tingly but I’m very happy you helped us feel good. Did we make you feel good too?” Rory asked him hopefully. He walked over to the tub and turned the water on after plugging the drain. 

“Don’t worry about me. I’m happy you two did. Now come on, let’s get you clean…” he told them. The two nodded and let him get to work on cleaning them. Thankfully, the two of them were much more calm than when they arrived, most notably Rory. Anne was already laid back but Rory wasn’t. So for her to be this relaxed was a god send. 

In record time, he had the two clean like they had not even had sex. Rory and Anne sat on the counter and continued yawning tiredly as he worked on drying off the shinx. It took much more effort because of her fur than it did Anne’s dry skin. When they were as dry as they would get, he picked them up and carried them to the living room and sat them on the couch where the two almost immediately passed out together. He wished he’d shown them how to help the other feel good but they weren’t dumb pokémon - they’d be able to figure it out.

Not even a few minutes later, there was a knock on Cole’s front door. When he opened it, he saw the owner of the two pokémon standing there. “Hey, come on in. They just fell asleep,” he told him with a chuckle. The guy gave a small chuckle in response and followed Cole to the living room and saw them sleeping, just as he said.

“Play too much?” he asked.

“Just a bit. We had a mess with paint and I had to give them a bath, I hope you don’t mind,” he told him. Little did the guy know it was a different type of paint they messed with.

“Not at all,” he told Cole. Reaching into his pocket, the guy pulled out a wad of money and handed it to him. He graciously accepted the money. He couldn’t help but laugh at himself for taking money after just having sex with his young pokémon. It was like he was being paid to fuck them. Now that would be the dream. The guy then pulled out two poké balls and recalled the pokémon. “I can’t thank you again for watching them on such short notice. A lot of people would turn me down. Mind watching them again sometime?”

“I’d love to see them again! They’re great friends with Sara and Tori so if I could get all four together for a play date, I think it’d be a lot of fun for them. I mean, if you’d be fine with that,” he said. The guy didn’t mind but Cole felt he’d have a problem if he knew what Cole was meaning with that. All four of his favorite little girls ready for him… he could hardly wait.

“Seems fine by me. We’ll discuss it later. Thanks again!” the guy said. Cole nodded and walked with the guy to the door before letting him out. Once gone, Cole sighed deeply. 

“God I fucking love babysitting…”


End file.
